diff --git a/.github/workflows/proto-check.yml b/.github/workflows/proto-check.yml
index c7e24af..25de234 100644
--- a/.github/workflows/proto-check.yml
+++ b/.github/workflows/proto-check.yml
@@ -7,12 +7,16 @@ on:
       - 'proto/**'
       - 'python/amplifier_core/_grpc_gen/**'
       - 'crates/amplifier-core/src/generated/**'
+      - 'scripts/generate_grpc_stubs.py'
+      - '.github/workflows/proto-check.yml'
   pull_request:
     branches: [main]
     paths:
       - 'proto/**'
       - 'python/amplifier_core/_grpc_gen/**'
       - 'crates/amplifier-core/src/generated/**'
+      - 'scripts/generate_grpc_stubs.py'
+      - '.github/workflows/proto-check.yml'
 
 jobs:
   proto-sync:
@@ -32,32 +36,18 @@ jobs:
           python-version: '3.12'
 
       - name: Install grpcio-tools
-        run: pip install grpcio-tools
+        run: pip install grpcio-tools==1.78.0
 
       - name: Regenerate Python stubs
         run: |
-          mkdir -p /tmp/proto_check
-          python -m grpc_tools.protoc \
-            -Iproto \
-            --python_out=/tmp/proto_check \
-            --grpc_python_out=/tmp/proto_check \
-            proto/amplifier_module.proto
+          python scripts/generate_grpc_stubs.py --output /tmp/proto_check
 
       - name: Compare with committed stubs
         run: |
-          # Check that key message classes exist in regenerated output
-          python -c "
-          import importlib.util, sys
-          spec = importlib.util.spec_from_file_location('pb2', '/tmp/proto_check/amplifier_module_pb2.py')
-          mod = importlib.util.module_from_spec(spec)
-          spec.loader.exec_module(mod)
-          required = ['ChatRequest', 'ChatResponse', 'ToolResult', 'HookResult', 'ModuleInfo']
-          missing = [t for t in required if not hasattr(mod, t)]
-          if missing:
-              print(f'FAIL: Missing types in regenerated stubs: {missing}')
-              sys.exit(1)
-          print('PASS: Regenerated stubs contain all required types')
-          "
+          diff -u python/amplifier_core/_grpc_gen/amplifier_module_pb2.py \
+            /tmp/proto_check/amplifier_module_pb2.py
+          diff -u python/amplifier_core/_grpc_gen/amplifier_module_pb2_grpc.py \
+            /tmp/proto_check/amplifier_module_pb2_grpc.py
 
   rust-build:
     name: Rust build and test
diff --git a/README.md b/README.md
index a9c65f8..3f76052 100644
--- a/README.md
+++ b/README.md
@@ -112,6 +112,14 @@ maturin develop
 uv run maturin develop
 ```
 
+To regenerate the committed Python gRPC stubs, install the pinned generator
+and run the canonical command:
+
+```bash
+python -m pip install grpcio-tools==1.78.0
+python scripts/generate_grpc_stubs.py
+```
+
 See [docs/RUST_CORE_TESTING.md](docs/RUST_CORE_TESTING.md) for the full development setup guide.
 
 **Build dependencies**: Rust 1.70+, maturin
diff --git a/bindings/node/index.d.ts b/bindings/node/index.d.ts
index b06fa5d..12f6e39 100644
--- a/bindings/node/index.d.ts
+++ b/bindings/node/index.d.ts
@@ -31,6 +31,14 @@ export const enum UserMessageLevel {
   Warning = 'Warning',
   Error = 'Error'
 }
+export interface JsContextInjection {
+  content: string
+  role: ContextInjectionRole
+  ephemeral: boolean
+  appendToLastToolResult: boolean
+  hookName: string
+  event: string
+}
 export interface JsHookResult {
   action: HookAction
   reason?: string
@@ -44,6 +52,7 @@ export interface JsHookResult {
   approvalPrompt?: string
   approvalTimeout?: number
   approvalDefault?: ApprovalDefault
+  contextInjections?: Array<JsContextInjection>
 }
 /** Structured error object returned to JS with a typed `code` property. */
 export interface JsAmplifierError {
diff --git a/bindings/node/src/hook_result.rs b/bindings/node/src/hook_result.rs
index f0a528d..4c94bde 100644
--- a/bindings/node/src/hook_result.rs
+++ b/bindings/node/src/hook_result.rs
@@ -2,10 +2,20 @@
 // Structs — exported as TypeScript interfaces via #[napi(object)]
 // ---------------------------------------------------------------------------
 
-use amplifier_core::models::HookResult;
+use amplifier_core::models::{ContextInjection, HookResult};
 
 use crate::enums::{ApprovalDefault, ContextInjectionRole, HookAction, UserMessageLevel};
 
+#[napi(object)]
+pub struct JsContextInjection {
+    pub content: String,
+    pub role: ContextInjectionRole,
+    pub ephemeral: bool,
+    pub append_to_last_tool_result: bool,
+    pub hook_name: String,
+    pub event: String,
+}
+
 #[napi(object)]
 pub struct JsHookResult {
     pub action: HookAction,
@@ -20,6 +30,7 @@ pub struct JsHookResult {
     pub approval_prompt: Option<String>,
     pub approval_timeout: Option<f64>,
     pub approval_default: Option<ApprovalDefault>,
+    pub context_injections: Option<Vec<JsContextInjection>>,
 }
 
 // ---------------------------------------------------------------------------
@@ -40,5 +51,23 @@ pub(crate) fn hook_result_to_js(result: HookResult) -> JsHookResult {
         approval_prompt: result.approval_prompt,
         approval_timeout: Some(result.approval_timeout),
         approval_default: Some(result.approval_default.into()),
+        context_injections: Some(
+            result
+                .context_injections
+                .into_iter()
+                .map(context_injection_to_js)
+                .collect(),
+        ),
+    }
+}
+
+fn context_injection_to_js(injection: ContextInjection) -> JsContextInjection {
+    JsContextInjection {
+        content: injection.content,
+        role: injection.role.into(),
+        ephemeral: injection.ephemeral,
+        append_to_last_tool_result: injection.append_to_last_tool_result,
+        hook_name: injection.hook_name,
+        event: injection.event,
     }
 }
diff --git a/bindings/node/src/lib.rs b/bindings/node/src/lib.rs
index 3e4f5f2..9f5b196 100644
--- a/bindings/node/src/lib.rs
+++ b/bindings/node/src/lib.rs
@@ -33,7 +33,7 @@ pub use enums::{
     ApprovalDefault, ContextInjectionRole, HookAction, SessionState, UserMessageLevel,
 };
 pub use errors::{amplifier_error_to_js, JsAmplifierError};
-pub use hook_result::JsHookResult;
+pub use hook_result::{JsContextInjection, JsHookResult};
 pub use hooks::JsHookRegistry;
 pub use module_resolver::{load_wasm_from_path, resolve_module, JsModuleManifest};
 pub use session::JsAmplifierSession;
diff --git a/bindings/python/src/coordinator/hook_dispatch.rs b/bindings/python/src/coordinator/hook_dispatch.rs
index ffa8b40..e5baba6 100644
--- a/bindings/python/src/coordinator/hook_dispatch.rs
+++ b/bindings/python/src/coordinator/hook_dispatch.rs
@@ -34,6 +34,16 @@ fn truncate_for_log(s: &str, max_chars: usize) -> String {
     }
 }
 
+struct PreparedInjection {
+    content: String,
+    role: String,
+    ephemeral: bool,
+    append_to_last_tool_result: bool,
+    hook_name: String,
+    event: String,
+    tokens: usize,
+}
+
 #[pymethods]
 impl PyCoordinator {
     /// Process a HookResult and route actions to appropriate subsystems.
@@ -118,6 +128,10 @@ impl PyCoordinator {
         let approval_timeout: f64 = result.getattr("approval_timeout")?.extract()?;
         let approval_default: String = result.getattr("approval_default")?.extract()?;
 
+        if action == "inject_context" {
+            return self.process_context_injections(py, result, event, hook_name);
+        }
+
         // Read coordinator config
         let size_limit: Option<usize> = {
             let val = self.get_injection_size_limit(py)?;
@@ -505,6 +519,296 @@ impl PyCoordinator {
 }
 
 impl PyCoordinator {
+    fn process_context_injections<'py>(
+        &mut self,
+        py: Python<'py>,
+        result: Bound<'py, PyAny>,
+        event: String,
+        hook_name: &str,
+    ) -> PyResult<Bound<'py, PyAny>> {
+        let scalar_content: Option<String> = {
+            let value = result.getattr("context_injection")?;
+            (!value.is_none()).then(|| value.extract()).transpose()?
+        };
+        let scalar_role: String = result.getattr("context_injection_role")?.extract()?;
+        let scalar_ephemeral: bool = result.getattr("ephemeral")?.extract()?;
+        let scalar_append: bool = result.getattr("append_to_last_tool_result")?.extract()?;
+        let suppress_output: bool = result.getattr("suppress_output")?.extract()?;
+        let user_message: Option<String> = {
+            let value = result.getattr("user_message")?;
+            (!value.is_none()).then(|| value.extract()).transpose()?
+        };
+        let user_message_level: String = result.getattr("user_message_level")?.extract()?;
+        let user_message_source: Option<String> = {
+            let value = result.getattr("user_message_source")?;
+            (!value.is_none()).then(|| value.extract()).transpose()?
+        };
+
+        let size_limit: Option<usize> = {
+            let value = self.get_injection_size_limit(py)?;
+            (!value.bind(py).is_none())
+                .then(|| value.extract(py))
+                .transpose()?
+        };
+        let budget: Option<usize> = {
+            let value = self.get_injection_budget_per_turn(py)?;
+            (!value.bind(py).is_none())
+                .then(|| value.extract(py))
+                .transpose()?
+        };
+
+        let items = result.getattr("context_injections")?;
+        let mut raw_items = Vec::new();
+        for item in items.try_iter()? {
+            let item = item?;
+            raw_items.push((
+                item.getattr("content")?.extract::<String>()?,
+                item.getattr("role")?.extract::<String>()?,
+                item.getattr("ephemeral")?.extract::<bool>()?,
+                item.getattr("append_to_last_tool_result")?
+                    .extract::<bool>()?,
+                item.getattr("hook_name")?.extract::<String>()?,
+                item.getattr("event")?.extract::<String>()?,
+            ));
+        }
+
+        // Scalar-only results predate the structured carrier. Normalize them
+        // here for direct callers that have not passed through HookRegistry.
+        if raw_items.is_empty() {
+            if let Some(content) = scalar_content {
+                raw_items.push((
+                    content,
+                    scalar_role,
+                    scalar_ephemeral,
+                    scalar_append,
+                    hook_name.to_string(),
+                    event.clone(),
+                ));
+            }
+        }
+
+        const CHARS_PER_TOKEN_ESTIMATE: usize = 4;
+        let sanitize = py
+            .import("amplifier_core.models")?
+            .getattr("_sanitize_for_llm")?;
+        let mut prepared = Vec::new();
+        for (content, role, ephemeral, append, item_hook_name, item_event) in raw_items {
+            let sanitized_content: String = sanitize
+                .call1((content,))?
+                .extract()
+                .map_err(|error| {
+                    log::error!(
+                        "SECURITY: Sanitization unavailable for hook '{}' — rejecting injection: {error}",
+                        item_hook_name
+                    );
+                    PyValueError::new_err(
+                        "Context injection rejected: content sanitization function unavailable",
+                    )
+                })?;
+            if sanitized_content.is_empty() {
+                continue;
+            }
+            let char_count = sanitized_content.chars().count();
+            if let Some(limit) = size_limit {
+                if char_count > limit {
+                    log::error!(
+                        "Hook injection too large: {} (chars={}, limit={})",
+                        item_hook_name,
+                        char_count,
+                        limit
+                    );
+                    return Err(PyValueError::new_err(format!(
+                        "Context injection exceeds {} characters",
+                        limit
+                    )));
+                }
+            }
+            prepared.push(PreparedInjection {
+                content: sanitized_content,
+                role,
+                ephemeral,
+                append_to_last_tool_result: append,
+                hook_name: item_hook_name,
+                event: item_event,
+                tokens: char_count / CHARS_PER_TOKEN_ESTIMATE,
+            });
+        }
+
+        // Every item is validated before the budget state is charged or any
+        // context write begins. Budget is still advisory, as it was for the
+        // legacy scalar path, but applies to the total item sequence.
+        let mut running_total = self.current_turn_injections;
+        for item in &prepared {
+            if let Some(limit) = budget {
+                if running_total + item.tokens > limit {
+                    log::warn!(
+                        "Warning: Hook injection budget exceeded \
+                         (hook={}, current={}, attempted={}, budget={})",
+                        item.hook_name,
+                        running_total,
+                        item.tokens,
+                        limit
+                    );
+                }
+            }
+            running_total += item.tokens;
+        }
+        self.current_turn_injections = running_total;
+
+        let context_obj: Py<PyAny> = {
+            let mount_points = self.mount_points.bind(py);
+            match mount_points.get_item("context")? {
+                Some(context) if !context.is_none() => context.unbind(),
+                _ => py.None(),
+            }
+        };
+        let has_context = {
+            let context = context_obj.bind(py);
+            !context.is_none() && context.hasattr("add_message")?
+        };
+
+        let now = if has_context && prepared.iter().any(|item| !item.ephemeral) {
+            let datetime = py.import("datetime")?;
+            let utc = datetime.getattr("timezone")?.getattr("utc")?;
+            Some(
+                datetime
+                    .getattr("datetime")?
+                    .call_method1("now", (utc,))?
+                    .call_method0("isoformat")?
+                    .unbind(),
+            )
+        } else {
+            None
+        };
+
+        let mut messages = Vec::new();
+        let mut residual = Vec::new();
+        for item in prepared {
+            log::info!(
+                "Hook context injection \
+                 (hook={}, event={}, chars={}, role={}, tokens={}, ephemeral={})",
+                item.hook_name,
+                item.event,
+                item.content.chars().count(),
+                item.role,
+                item.tokens,
+                item.ephemeral
+            );
+            if item.ephemeral {
+                residual.push(item);
+                continue;
+            }
+            if has_context {
+                let metadata = PyDict::new(py);
+                metadata.set_item("source", "hook")?;
+                metadata.set_item("hook_name", &item.hook_name)?;
+                metadata.set_item("event", &item.event)?;
+                metadata.set_item("timestamp", now.as_ref().unwrap().bind(py))?;
+                metadata.set_item("requested_role", &item.role)?;
+                metadata.set_item("ephemeral", false)?;
+                metadata.set_item("persisted", true)?;
+
+                let message = PyDict::new(py);
+                message.set_item("role", &item.role)?;
+                message.set_item("content", &item.content)?;
+                message.set_item("metadata", metadata)?;
+                messages.push(message.into_any().unbind());
+            }
+        }
+
+        if let Some(message) = user_message.filter(|message| !message.is_empty()) {
+            let source = user_message_source.as_deref().unwrap_or(hook_name);
+            let display = self.display_system_obj.bind(py);
+            if display.is_none() {
+                log::debug!(
+                    "Hook message ({}): {} (hook={})",
+                    user_message_level,
+                    truncate_for_log(&message, 200),
+                    source
+                );
+            } else if let Err(error) = display.call_method(
+                "show_message",
+                (&message, &user_message_level, format!("hook:{source}")),
+                None,
+            ) {
+                log::error!("Error calling display_system: {error}");
+            }
+        }
+        if suppress_output {
+            log::debug!("Hook '{}' requested output suppression", hook_name);
+        }
+
+        let result_py = result.unbind();
+        let hook_result_cls = py
+            .import("amplifier_core.models")?
+            .getattr("HookResult")?
+            .unbind();
+        wrap_future_as_coroutine(
+            py,
+            pyo3_async_runtimes::tokio::future_into_py(py, async move {
+                let bridge = PyContextManagerBridge {
+                    py_obj: context_obj,
+                };
+                for message in messages {
+                    bridge.add_message(message).await?;
+                }
+                Self::make_residual_hook_result(&hook_result_cls, &result_py, &residual)
+            }),
+        )
+    }
+
+    fn make_residual_hook_result(
+        hook_result_cls: &Py<PyAny>,
+        original: &Py<PyAny>,
+        residual: &[PreparedInjection],
+    ) -> PyResult<Py<PyAny>> {
+        Python::try_attach(|py| -> PyResult<Py<PyAny>> {
+            let values = original.call_method0(py, "model_dump")?;
+            let updates = PyDict::new(py);
+            let injections = pyo3::types::PyList::empty(py);
+            for item in residual {
+                let injection = PyDict::new(py);
+                injection.set_item("content", &item.content)?;
+                injection.set_item("role", &item.role)?;
+                injection.set_item("ephemeral", item.ephemeral)?;
+                injection.set_item(
+                    "append_to_last_tool_result",
+                    item.append_to_last_tool_result,
+                )?;
+                injection.set_item("hook_name", &item.hook_name)?;
+                injection.set_item("event", &item.event)?;
+                injections.append(injection)?;
+            }
+            updates.set_item("context_injections", injections)?;
+            if residual.is_empty() {
+                updates.set_item("action", "continue")?;
+                updates.set_item("context_injection", py.None())?;
+                updates.set_item("context_injection_role", "system")?;
+                updates.set_item("ephemeral", false)?;
+                updates.set_item("append_to_last_tool_result", false)?;
+            } else {
+                updates.set_item("action", "inject_context")?;
+                updates.set_item(
+                    "context_injection",
+                    residual
+                        .iter()
+                        .map(|item| item.content.as_str())
+                        .collect::<Vec<_>>()
+                        .join("\n\n"),
+                )?;
+                updates.set_item("context_injection_role", &residual[0].role)?;
+                updates.set_item("ephemeral", true)?;
+                updates.set_item(
+                    "append_to_last_tool_result",
+                    residual.iter().any(|item| item.append_to_last_tool_result),
+                )?;
+            }
+            values.call_method1(py, "update", (updates,))?;
+            hook_result_cls.call_method1(py, "model_validate", (values,))
+        })
+        .ok_or_else(|| PyRuntimeError::new_err("Failed to create residual HookResult"))?
+    }
+
     /// Construct a HookResult Python object with the given action and optional reason.
     ///
     /// Centralises the `Python::try_attach` + `PyDict` + `hook_result_cls.call` pattern
diff --git a/crates/amplifier-core/src/bridges/grpc_hook.rs b/crates/amplifier-core/src/bridges/grpc_hook.rs
index 5a7fa7d..0a1f8cb 100644
--- a/crates/amplifier-core/src/bridges/grpc_hook.rs
+++ b/crates/amplifier-core/src/bridges/grpc_hook.rs
@@ -194,6 +194,35 @@ impl GrpcHookBridge {
                 }
             };
 
+        let context_injections = proto
+            .context_injections
+            .into_iter()
+            .map(|injection| {
+                let role = match amplifier_module::ContextInjectionRole::try_from(injection.role) {
+                    Ok(amplifier_module::ContextInjectionRole::System) => {
+                        models::ContextInjectionRole::System
+                    }
+                    Ok(amplifier_module::ContextInjectionRole::User) => {
+                        models::ContextInjectionRole::User
+                    }
+                    Ok(amplifier_module::ContextInjectionRole::Assistant) => {
+                        models::ContextInjectionRole::Assistant
+                    }
+                    Ok(amplifier_module::ContextInjectionRole::Unspecified) | Err(_) => {
+                        models::ContextInjectionRole::System
+                    }
+                };
+                models::ContextInjection {
+                    content: injection.content,
+                    role,
+                    ephemeral: injection.ephemeral,
+                    append_to_last_tool_result: injection.append_to_last_tool_result,
+                    hook_name: injection.hook_name,
+                    event: injection.event,
+                }
+            })
+            .collect();
+
         let approval_prompt = if proto.approval_prompt.is_empty() {
             None
         } else {
@@ -267,6 +296,7 @@ impl GrpcHookBridge {
             user_message_level,
             user_message_source,
             append_to_last_tool_result: proto.append_to_last_tool_result,
+            context_injections,
             extensions: HashMap::new(),
         }
     }
@@ -333,6 +363,7 @@ mod tests {
             user_message_level: 0,
             user_message_source: String::new(),
             append_to_last_tool_result: false,
+            context_injections: vec![],
         }
     }
 
diff --git a/crates/amplifier-core/src/generated/amplifier.module.rs b/crates/amplifier-core/src/generated/amplifier.module.rs
index d510a11..b280ae7 100644
--- a/crates/amplifier-core/src/generated/amplifier.module.rs
+++ b/crates/amplifier-core/src/generated/amplifier.module.rs
@@ -405,6 +405,21 @@ pub struct ToolResult {
     pub error_json: ::prost::alloc::string::String,
 }
 #[derive(Clone, PartialEq, ::prost::Message)]
+pub struct ContextInjection {
+    #[prost(string, tag = "1")]
+    pub content: ::prost::alloc::string::String,
+    #[prost(enumeration = "ContextInjectionRole", tag = "2")]
+    pub role: i32,
+    #[prost(bool, tag = "3")]
+    pub ephemeral: bool,
+    #[prost(bool, tag = "4")]
+    pub append_to_last_tool_result: bool,
+    #[prost(string, tag = "5")]
+    pub hook_name: ::prost::alloc::string::String,
+    #[prost(string, tag = "6")]
+    pub event: ::prost::alloc::string::String,
+}
+#[derive(Clone, PartialEq, ::prost::Message)]
 pub struct HookResult {
     #[prost(enumeration = "HookAction", tag = "1")]
     pub action: i32,
@@ -437,6 +452,8 @@ pub struct HookResult {
     pub user_message_source: ::prost::alloc::string::String,
     #[prost(bool, tag = "15")]
     pub append_to_last_tool_result: bool,
+    #[prost(message, repeated, tag = "16")]
+    pub context_injections: ::prost::alloc::vec::Vec<ContextInjection>,
 }
 #[derive(Clone, PartialEq, ::prost::Message)]
 pub struct ModelInfo {
diff --git a/crates/amplifier-core/src/generated/conversions.rs b/crates/amplifier-core/src/generated/conversions.rs
index 39b06cf..fdc8ae3 100644
--- a/crates/amplifier-core/src/generated/conversions.rs
+++ b/crates/amplifier-core/src/generated/conversions.rs
@@ -602,6 +602,27 @@ pub fn native_hook_result_to_proto(
         .map(|d| to_json_or_warn(d, "HookResult data"))
         .unwrap_or_default();
 
+    let context_injections = result
+        .context_injections
+        .iter()
+        .map(|injection| amplifier_module::ContextInjection {
+            content: injection.content.clone(),
+            role: match injection.role {
+                ContextInjectionRole::System => {
+                    amplifier_module::ContextInjectionRole::System as i32
+                }
+                ContextInjectionRole::User => amplifier_module::ContextInjectionRole::User as i32,
+                ContextInjectionRole::Assistant => {
+                    amplifier_module::ContextInjectionRole::Assistant as i32
+                }
+            },
+            ephemeral: injection.ephemeral,
+            append_to_last_tool_result: injection.append_to_last_tool_result,
+            hook_name: injection.hook_name.clone(),
+            event: injection.event.clone(),
+        })
+        .collect();
+
     amplifier_module::HookResult {
         action,
         data_json,
@@ -618,6 +639,7 @@ pub fn native_hook_result_to_proto(
         user_message_level,
         user_message_source: result.user_message_source.clone().unwrap_or_default(),
         append_to_last_tool_result: result.append_to_last_tool_result,
+        context_injections,
     }
 }
 
@@ -2289,7 +2311,8 @@ mod tests {
     fn hook_result_roundtrip_via_bridge_reverse() {
         use crate::bridges::grpc_hook::GrpcHookBridge;
         use crate::models::{
-            ApprovalDefault, ContextInjectionRole, HookAction, HookResult, UserMessageLevel,
+            ApprovalDefault, ContextInjection, ContextInjectionRole, HookAction, HookResult,
+            UserMessageLevel,
         };
 
         let original = HookResult {
@@ -2308,6 +2331,14 @@ mod tests {
             user_message_level: UserMessageLevel::Warning,
             user_message_source: Some("approval-hook".to_string()),
             append_to_last_tool_result: false,
+            context_injections: vec![ContextInjection {
+                content: "ordered injection".to_string(),
+                role: ContextInjectionRole::Assistant,
+                ephemeral: true,
+                append_to_last_tool_result: true,
+                hook_name: "registered-hook".to_string(),
+                event: "tool:post".to_string(),
+            }],
             extensions: HashMap::new(),
         };
 
@@ -2334,6 +2365,7 @@ mod tests {
             restored.append_to_last_tool_result,
             original.append_to_last_tool_result
         );
+        assert_eq!(restored.context_injections, original.context_injections);
     }
 
     #[test]
diff --git a/crates/amplifier-core/src/generated/equivalence_tests.rs b/crates/amplifier-core/src/generated/equivalence_tests.rs
index 87b4775..9a844fa 100644
--- a/crates/amplifier-core/src/generated/equivalence_tests.rs
+++ b/crates/amplifier-core/src/generated/equivalence_tests.rs
@@ -59,7 +59,7 @@ mod tests {
     }
 
     #[test]
-    fn proto_hook_result_has_all_15_fields() {
+    fn proto_hook_result_has_all_16_fields() {
         let result = HookResult {
             action: HookAction::Modify as i32,
             data_json: r#"{"modified": true}"#.into(),
@@ -76,6 +76,7 @@ mod tests {
             user_message_level: UserMessageLevel::Warning as i32,
             user_message_source: "content-filter".into(),
             append_to_last_tool_result: true,
+            context_injections: vec![],
         };
         assert_eq!(result.action, HookAction::Modify as i32);
         assert_eq!(result.data_json, r#"{"modified": true}"#);
diff --git a/crates/amplifier-core/src/hooks.rs b/crates/amplifier-core/src/hooks.rs
index d10b113..3f115ff 100644
--- a/crates/amplifier-core/src/hooks.rs
+++ b/crates/amplifier-core/src/hooks.rs
@@ -31,7 +31,7 @@ use std::time::Duration;
 
 use serde_json::Value;
 
-use crate::models::{HookAction, HookResult};
+use crate::models::{ContextInjection, HookAction, HookResult};
 use crate::traits::HookHandler;
 
 // ---------------------------------------------------------------------------
@@ -209,7 +209,7 @@ impl HookRegistry {
         let mut inject_context_results: Vec<HookResult> = Vec::new();
 
         for (handler, name) in &entries {
-            let result = match handler.handle(event, current_data.clone()).await {
+            let mut result = match handler.handle(event, current_data.clone()).await {
                 Ok(r) => r,
                 Err(e) => {
                     // Error in handler -- log and continue (matches Python behaviour).
@@ -222,6 +222,8 @@ impl HookRegistry {
                 }
             };
 
+            normalize_inject_context_result(&mut result, name, event);
+
             // Deny short-circuits immediately
             if result.action == HookAction::Deny {
                 return result;
@@ -241,7 +243,7 @@ impl HookRegistry {
             }
 
             // Collect inject_context for merging at end
-            if result.action == HookAction::InjectContext && result.context_injection.is_some() {
+            if result.action == HookAction::InjectContext && !result.context_injections.is_empty() {
                 inject_context_results.push(result.clone());
             }
 
@@ -402,58 +404,111 @@ fn value_to_map(value: &Value) -> HashMap<String, Value> {
 
 /// Merge multiple inject_context HookResults into a single result.
 ///
-/// Combines injections with `"\n\n"` separator. `context_injection_role` and
-/// `suppress_output` are taken from the first result (these are display/role
-/// settings where "first wins" is a reasonable, harmless default). `ephemeral`
-/// and `append_to_last_tool_result` instead use OR semantics across ALL
-/// results, not just the first:
-///
-/// `ephemeral` in particular MUST be the logical OR of every contributing
-/// result, not `first.ephemeral`. The combined `context_injection` string is
-/// the concatenation of every hook's content -- if even one of those hooks
-/// marked its own contribution `ephemeral: true` (regenerated per turn), the
-/// resulting combined string is regenerated per turn too, byte-for-byte
-/// identical only when ALL contributors are stable. Taking only the first
-/// result's `ephemeral` flag meant a single non-ephemeral hook running before
-/// an ephemeral one (pure registration-order luck) would silently downgrade
-/// the merged result to `ephemeral: false` -- causing every downstream
-/// consumer that trusts `Message.metadata["ephemeral"]` (e.g. the Anthropic
-/// provider's conversation-region prompt-cache breakpoint placement) to lose
-/// the ephemeral signal for the ENTIRE combined injection, not just the
-/// stable part. See amplifier_module_provider_anthropic's
-/// `_count_trailing_ephemeral_messages` / `_apply_conversation_cache_control`.
+/// Keeps the ordered list lossless and projects the legacy scalar fields from
+/// every item: bodies are joined with `"\n\n"`, the first role wins, and both
+/// boolean flags use OR semantics.
 fn merge_inject_context_results(results: &[HookResult]) -> HookResult {
     if results.is_empty() {
         return HookResult::default();
     }
 
-    if results.len() == 1 {
-        return results[0].clone();
+    let context_injections: Vec<ContextInjection> = results
+        .iter()
+        .flat_map(|result| {
+            if result.context_injections.is_empty() {
+                result
+                    .context_injection
+                    .as_ref()
+                    .map(|content| {
+                        vec![ContextInjection {
+                            content: content.clone(),
+                            role: result.context_injection_role.clone(),
+                            ephemeral: result.ephemeral,
+                            append_to_last_tool_result: result.append_to_last_tool_result,
+                            hook_name: "unknown".to_string(),
+                            event: String::new(),
+                        }]
+                    })
+                    .unwrap_or_default()
+            } else {
+                result.context_injections.clone()
+            }
+        })
+        .collect();
+
+    if context_injections.is_empty() {
+        return HookResult::default();
     }
 
-    // Combine all injections
-    let combined_content: String = results
+    let combined_content = context_injections
         .iter()
-        .filter_map(|r| r.context_injection.as_deref())
+        .map(|injection| injection.content.as_str())
         .collect::<Vec<_>>()
         .join("\n\n");
-
-    // role/suppress_output: "first wins" -- harmless display-only settings.
     let first = &results[0];
+    let first_injection = &context_injections[0];
+
+    // A single handler may return multiple structured injections.  This is
+    // normalization, not aggregation: retain the handler's other result-level
+    // fields (including UI and approval metadata) while updating only the
+    // legacy injection projection.
+    if results.len() == 1 {
+        let mut result = first.clone();
+        result.action = HookAction::InjectContext;
+        result.context_injection = Some(combined_content);
+        result.context_injection_role = first_injection.role.clone();
+        result.ephemeral = context_injections
+            .iter()
+            .any(|injection| injection.ephemeral);
+        result.append_to_last_tool_result = context_injections
+            .iter()
+            .any(|injection| injection.append_to_last_tool_result);
+        result.context_injections = context_injections;
+        return result;
+    }
 
     HookResult {
         action: HookAction::InjectContext,
         context_injection: Some(combined_content),
-        context_injection_role: first.context_injection_role.clone(),
-        // OR semantics: ANY contributing result marking itself ephemeral
-        // makes the whole merged injection ephemeral (see doc comment above).
-        ephemeral: results.iter().any(|r| r.ephemeral),
+        context_injection_role: first_injection.role.clone(),
+        ephemeral: context_injections
+            .iter()
+            .any(|injection| injection.ephemeral),
         suppress_output: first.suppress_output,
-        append_to_last_tool_result: results.iter().any(|r| r.append_to_last_tool_result),
+        append_to_last_tool_result: context_injections
+            .iter()
+            .any(|injection| injection.append_to_last_tool_result),
+        context_injections,
         ..Default::default()
     }
 }
 
+/// Bind injection provenance at the trusted registration boundary and promote
+/// legacy scalar injections into the structured carrier.
+fn normalize_inject_context_result(result: &mut HookResult, handler_name: &str, event: &str) {
+    if result.action != HookAction::InjectContext {
+        return;
+    }
+
+    if result.context_injections.is_empty() {
+        if let Some(content) = result.context_injection.clone() {
+            result.context_injections.push(ContextInjection {
+                content,
+                role: result.context_injection_role.clone(),
+                ephemeral: result.ephemeral,
+                append_to_last_tool_result: result.append_to_last_tool_result,
+                hook_name: handler_name.to_string(),
+                event: event.to_string(),
+            });
+        }
+    }
+
+    for injection in &mut result.context_injections {
+        injection.hook_name = handler_name.to_string();
+        injection.event = event.to_string();
+    }
+}
+
 // ---------------------------------------------------------------------------
 // Tests
 // ---------------------------------------------------------------------------
@@ -830,6 +885,91 @@ mod tests {
         assert!(injection.contains("second injection"));
     }
 
+    #[tokio::test]
+    async fn single_structured_injection_result_preserves_non_injection_fields() {
+        use crate::models::{ApprovalDefault, ContextInjectionRole, UserMessageLevel};
+
+        let registry = HookRegistry::new();
+        let original_data = HashMap::from([("keep".to_string(), serde_json::json!(true))]);
+        let original_extensions =
+            HashMap::from([("future_field".to_string(), serde_json::json!("preserved"))]);
+        let handler = Arc::new(SimpleHandler(HookResult {
+            action: HookAction::InjectContext,
+            data: Some(original_data.clone()),
+            reason: Some("keep reason".into()),
+            // The scalar fields are intentionally stale: the list is canonical.
+            context_injection: Some("stale scalar".into()),
+            context_injection_role: ContextInjectionRole::System,
+            ephemeral: false,
+            approval_prompt: Some("keep approval".into()),
+            approval_options: Some(vec!["allow".into(), "deny".into()]),
+            approval_timeout: 42.0,
+            approval_default: ApprovalDefault::Allow,
+            suppress_output: true,
+            user_message: Some("Context injected".into()),
+            user_message_level: UserMessageLevel::Warning,
+            user_message_source: Some("status-context".into()),
+            append_to_last_tool_result: false,
+            context_injections: vec![
+                ContextInjection {
+                    content: "first".into(),
+                    role: ContextInjectionRole::User,
+                    ephemeral: false,
+                    append_to_last_tool_result: false,
+                    hook_name: "untrusted".into(),
+                    event: "untrusted".into(),
+                },
+                ContextInjection {
+                    content: "second".into(),
+                    role: ContextInjectionRole::Assistant,
+                    ephemeral: true,
+                    append_to_last_tool_result: true,
+                    hook_name: "untrusted".into(),
+                    event: "untrusted".into(),
+                },
+            ],
+            extensions: original_extensions.clone(),
+        }));
+        let _ = registry.register(
+            "test:structured",
+            handler,
+            0,
+            Some("structured-hook".into()),
+        );
+
+        let result = registry
+            .emit("test:structured", serde_json::json!({}))
+            .await;
+
+        assert_eq!(result.action, HookAction::InjectContext);
+        assert_eq!(result.context_injection.as_deref(), Some("first\n\nsecond"));
+        assert_eq!(result.context_injection_role, ContextInjectionRole::User);
+        assert!(result.ephemeral);
+        assert!(result.append_to_last_tool_result);
+        assert_eq!(result.context_injections.len(), 2);
+        assert_eq!(result.context_injections[0].hook_name, "structured-hook");
+        assert_eq!(result.context_injections[0].event, "test:structured");
+        assert_eq!(result.context_injections[1].hook_name, "structured-hook");
+        assert_eq!(result.context_injections[1].event, "test:structured");
+        assert_eq!(result.data, Some(original_data));
+        assert_eq!(result.reason.as_deref(), Some("keep reason"));
+        assert_eq!(result.approval_prompt.as_deref(), Some("keep approval"));
+        assert_eq!(
+            result.approval_options,
+            Some(vec!["allow".into(), "deny".into()])
+        );
+        assert_eq!(result.approval_timeout, 42.0);
+        assert_eq!(result.approval_default, ApprovalDefault::Allow);
+        assert!(result.suppress_output);
+        assert_eq!(result.user_message.as_deref(), Some("Context injected"));
+        assert_eq!(result.user_message_level, UserMessageLevel::Warning);
+        assert_eq!(
+            result.user_message_source.as_deref(),
+            Some("status-context")
+        );
+        assert_eq!(result.extensions, original_extensions);
+    }
+
     // ---------------------------------------------------------------
     // Unregister
     // ---------------------------------------------------------------
@@ -1257,6 +1397,39 @@ mod tests {
         );
     }
 
+    #[tokio::test]
+    async fn registered_mixed_legacy_injections_preserve_item_lifetime() {
+        let registry = HookRegistry::new();
+        let durable = Arc::new(SimpleHandler(HookResult {
+            action: HookAction::InjectContext,
+            context_injection: Some("durable".into()),
+            context_injection_role: crate::models::ContextInjectionRole::Assistant,
+            ephemeral: false,
+            ..Default::default()
+        }));
+        let temporary = Arc::new(SimpleHandler(HookResult {
+            action: HookAction::InjectContext,
+            context_injection: Some("temporary".into()),
+            context_injection_role: crate::models::ContextInjectionRole::User,
+            ephemeral: true,
+            ..Default::default()
+        }));
+
+        let _ = registry.register("test:mixed", durable, 0, Some("durable-hook".into()));
+        let _ = registry.register("test:mixed", temporary, 10, Some("temporary-hook".into()));
+
+        let result = registry.emit("test:mixed", serde_json::json!({})).await;
+        assert_eq!(result.context_injections.len(), 2);
+        assert_eq!(result.context_injections[0].content, "durable");
+        assert!(!result.context_injections[0].ephemeral);
+        assert_eq!(result.context_injections[0].hook_name, "durable-hook");
+        assert_eq!(result.context_injections[0].event, "test:mixed");
+        assert_eq!(result.context_injections[1].content, "temporary");
+        assert!(result.context_injections[1].ephemeral);
+        assert_eq!(result.context_injections[1].hook_name, "temporary-hook");
+        assert_eq!(result.context_injections[1].event, "test:mixed");
+    }
+
     /// Verify that the `log` crate is available and usable from amplifier-core.
     /// This ensures Rust code can emit structured log messages that will be
     /// routed through Python's logging module via pyo3-log in the bindings.
diff --git a/crates/amplifier-core/src/lib.rs b/crates/amplifier-core/src/lib.rs
index 3390987..3891f64 100644
--- a/crates/amplifier-core/src/lib.rs
+++ b/crates/amplifier-core/src/lib.rs
@@ -51,8 +51,8 @@ pub use errors::{AmplifierError, ContextError, HookError, ProviderError, Session
 // Core data models
 pub use models::{
     ApprovalDefault, ApprovalRequest, ApprovalResponse, ConfigField, ConfigFieldType,
-    ContextInjectionRole, HookAction, HookResult, ModelInfo, ModuleInfo, ModuleType, ProviderInfo,
-    SessionState, SessionStatus, ToolResult, UserMessageLevel,
+    ContextInjection, ContextInjectionRole, HookAction, HookResult, ModelInfo, ModuleInfo,
+    ModuleType, ProviderInfo, SessionState, SessionStatus, ToolResult, UserMessageLevel,
 };
 
 // Chat protocol models
diff --git a/crates/amplifier-core/src/models.rs b/crates/amplifier-core/src/models.rs
index 266c62e..6c3c50d 100644
--- a/crates/amplifier-core/src/models.rs
+++ b/crates/amplifier-core/src/models.rs
@@ -106,6 +106,40 @@ pub enum SessionState {
 // Structs
 // ---------------------------------------------------------------------------
 
+/// One independently processed context injection from a hook.
+///
+/// The registry binds `hook_name` and `event` from the registered handler that
+/// emitted this item. Consumers must not rely on handler-provided provenance.
+#[derive(Debug, Clone, PartialEq, Eq, Serialize, Deserialize)]
+pub struct ContextInjection {
+    /// Text to inject into the agent's conversation context.
+    pub content: String,
+
+    /// Role for the injected message in conversation.
+    #[serde(default)]
+    pub role: ContextInjectionRole,
+
+    /// Whether this injection is request-only rather than durable history.
+    #[serde(default)]
+    pub ephemeral: bool,
+
+    /// Carrier for post-tool-result placement; interpreted by the loop layer.
+    #[serde(default)]
+    pub append_to_last_tool_result: bool,
+
+    /// Registered handler name, bound by the hook registry.
+    #[serde(default = "default_unknown_hook_name")]
+    pub hook_name: String,
+
+    /// Event that emitted the injection, bound by the hook registry.
+    #[serde(default)]
+    pub event: String,
+}
+
+fn default_unknown_hook_name() -> String {
+    "unknown".to_string()
+}
+
 /// Result from hook execution with enhanced capabilities.
 ///
 /// Hooks can observe, block, modify operations, inject context to the agent,
@@ -187,6 +221,13 @@ pub struct HookResult {
     #[serde(default)]
     pub append_to_last_tool_result: bool,
 
+    /// Ordered, lossless context injection items.
+    ///
+    /// The legacy scalar context fields remain for backwards compatibility and
+    /// are projected from this list by the hook registry.
+    #[serde(default)]
+    pub context_injections: Vec<ContextInjection>,
+
     /// Extension fields for forward-compatibility.
     /// Captures any unknown JSON keys during deserialization.
     #[serde(flatten)]
@@ -215,6 +256,7 @@ impl Default for HookResult {
             user_message_level: UserMessageLevel::default(),
             user_message_source: None,
             append_to_last_tool_result: false,
+            context_injections: Vec::new(),
             extensions: HashMap::new(),
         }
     }
@@ -560,6 +602,23 @@ mod tests {
         assert!(result.context_injection.is_none());
         assert_eq!(result.context_injection_role, ContextInjectionRole::System);
         assert!(!result.ephemeral);
+        assert!(result.context_injections.is_empty());
+    }
+
+    #[test]
+    fn context_injection_serialization_roundtrip() {
+        let injection = ContextInjection {
+            content: "temporary reminder".into(),
+            role: ContextInjectionRole::User,
+            ephemeral: true,
+            append_to_last_tool_result: true,
+            hook_name: "registered-hook".into(),
+            event: "tool:post".into(),
+        };
+
+        let json = serde_json::to_string(&injection).unwrap();
+        let restored: ContextInjection = serde_json::from_str(&json).unwrap();
+        assert_eq!(restored, injection);
     }
 
     #[test]
diff --git a/proto/amplifier_module.proto b/proto/amplifier_module.proto
index e12f988..cd47b85 100644
--- a/proto/amplifier_module.proto
+++ b/proto/amplifier_module.proto
@@ -389,6 +389,15 @@ message ToolResult {
   string error_json  = 3;
 }
 
+message ContextInjection {
+  string               content                    = 1;
+  ContextInjectionRole role                       = 2;
+  bool                 ephemeral                  = 3;
+  bool                 append_to_last_tool_result = 4;
+  string               hook_name                  = 5;
+  string               event                      = 6;
+}
+
 message HookResult {
   HookAction           action                     = 1;
   string               data_json                  = 2;
@@ -406,6 +415,7 @@ message HookResult {
   UserMessageLevel     user_message_level         = 13;
   string               user_message_source        = 14;
   bool                 append_to_last_tool_result = 15;
+  repeated ContextInjection context_injections    = 16;
 }
 
 message ModelInfo {
diff --git a/python/amplifier_core/__init__.py b/python/amplifier_core/__init__.py
index b4e014c..ca80776 100644
--- a/python/amplifier_core/__init__.py
+++ b/python/amplifier_core/__init__.py
@@ -74,6 +74,7 @@
 from .message_models import ToolSpec
 from .message_models import Usage
 from .models import ConfigField
+from .models import ContextInjection
 from .models import HookResult
 from .models import ModelInfo
 from .models import ModuleInfo
@@ -114,6 +115,7 @@
     "HookRegistry",
     "ToolCall",
     "ToolResult",
+    "ContextInjection",
     "HookResult",
     "ConfigField",
     "ModelInfo",
diff --git a/python/amplifier_core/_grpc_gen/__init__.py b/python/amplifier_core/_grpc_gen/__init__.py
index 4b20486..8e32a4e 100644
--- a/python/amplifier_core/_grpc_gen/__init__.py
+++ b/python/amplifier_core/_grpc_gen/__init__.py
@@ -1,8 +1,5 @@
 """Generated gRPC stubs for amplifier_module.proto.
 
 Do not edit these files directly. Regenerate with:
-    python -m grpc_tools.protoc -I proto \
-        --python_out=python/amplifier_core/_grpc_gen \
-        --grpc_python_out=python/amplifier_core/_grpc_gen \
-        proto/amplifier_module.proto
+    python scripts/generate_grpc_stubs.py
 """
diff --git a/python/amplifier_core/_grpc_gen/amplifier_module_pb2.py b/python/amplifier_core/_grpc_gen/amplifier_module_pb2.py
index 6f4d751..f1ac9dd 100644
--- a/python/amplifier_core/_grpc_gen/amplifier_module_pb2.py
+++ b/python/amplifier_core/_grpc_gen/amplifier_module_pb2.py
@@ -24,7 +24,7 @@
 
 
 
-DESCRIPTOR = _descriptor_pool.Default().AddSerializedFile(b'\n\x16\x61mplifier_module.proto\x12\x10\x61mplifier.module\"\x07\n\x05\x45mpty\"F\n\x08ToolSpec\x12\x0c\n\x04name\x18\x01 \x01(\t\x12\x13\n\x0b\x64\x65scription\x18\x02 \x01(\t\x12\x17\n\x0fparameters_json\x18\x03 \x01(\t\"9\n\x12ToolExecuteRequest\x12\r\n\x05input\x18\x01 \x01(\x0c\x12\x14\n\x0c\x63ontent_type\x18\x02 \x01(\t\"[\n\x13ToolExecuteResponse\x12\x0f\n\x07success\x18\x01 \x01(\x08\x12\x0e\n\x06output\x18\x02 \x01(\x0c\x12\x14\n\x0c\x63ontent_type\x18\x03 \x01(\t\x12\r\n\x05\x65rror\x18\x04 \x01(\t\"\xd6\x01\n\nModuleInfo\x12\n\n\x02id\x18\x01 \x01(\t\x12\x0c\n\x04name\x18\x02 \x01(\t\x12\x0f\n\x07version\x18\x03 \x01(\t\x12\x31\n\x0bmodule_type\x18\x04 \x01(\x0e\x32\x1c.amplifier.module.ModuleType\x12\x13\n\x0bmount_point\x18\x05 \x01(\t\x12\x13\n\x0b\x64\x65scription\x18\x06 \x01(\t\x12\x1a\n\x12\x63onfig_schema_json\x18\x07 \x01(\t\x12\x14\n\x0c\x63\x61pabilities\x18\x08 \x03(\t\x12\x0e\n\x06\x61uthor\x18\t 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
 _globals = globals()
 _builder.BuildMessageAndEnumDescriptors(DESCRIPTOR, _globals)
@@ -35,30 +35,30 @@
   _globals['_MOUNTREQUEST_CONFIGENTRY']._serialized_options = b'8\001'
   _globals['_CONFIGFIELD_SHOWWHENENTRY']._loaded_options = None
   _globals['_CONFIGFIELD_SHOWWHENENTRY']._serialized_options = b'8\001'
-  _globals['_MODULETYPE']._serialized_start=7113
-  _globals['_MODULETYPE']._serialized_end=7301
-  _globals['_HEALTHSTATUS']._serialized_start=7304
-  _globals['_HEALTHSTATUS']._serialized_end=7434
-  _globals['_CONFIGFIELDTYPE']._serialized_start=7437
-  _globals['_CONFIGFIELDTYPE']._serialized_end=7610
-  _globals['_PROVIDERERRORTYPE']._serialized_start=7613
-  _globals['_PROVIDERERRORTYPE']._serialized_end=7957
-  _globals['_TOOLERRORTYPE']._serialized_start=7960
-  _globals['_TOOLERRORTYPE']._serialized_end=8100
-  _globals['_HOOKERRORTYPE']._serialized_start=8103
-  _globals['_HOOKERRORTYPE']._serialized_end=8243
-  _globals['_ROLE']._serialized_start=8246
-  _globals['_ROLE']._serialized_end=8380
-  _globals['_VISIBILITY']._serialized_start=8382
-  _globals['_VISIBILITY']._serialized_end=8493
-  _globals['_HOOKACTION']._serialized_start=8496
-  _globals['_HOOKACTION']._serialized_end=8667
-  _globals['_CONTEXTINJECTIONROLE']._serialized_start=8670
-  _globals['_CONTEXTINJECTIONROLE']._serialized_end=8838
-  _globals['_APPROVALDEFAULT']._serialized_start=8840
-  _globals['_APPROVALDEFAULT']._serialized_end=8948
-  _globals['_USERMESSAGELEVEL']._serialized_start=8951
-  _globals['_USERMESSAGELEVEL']._serialized_end=9096
+  _globals['_MODULETYPE']._serialized_start=7358
+  _globals['_MODULETYPE']._serialized_end=7546
+  _globals['_HEALTHSTATUS']._serialized_start=7549
+  _globals['_HEALTHSTATUS']._serialized_end=7679
+  _globals['_CONFIGFIELDTYPE']._serialized_start=7682
+  _globals['_CONFIGFIELDTYPE']._serialized_end=7855
+  _globals['_PROVIDERERRORTYPE']._serialized_start=7858
+  _globals['_PROVIDERERRORTYPE']._serialized_end=8202
+  _globals['_TOOLERRORTYPE']._serialized_start=8205
+  _globals['_TOOLERRORTYPE']._serialized_end=8345
+  _globals['_HOOKERRORTYPE']._serialized_start=8348
+  _globals['_HOOKERRORTYPE']._serialized_end=8488
+  _globals['_ROLE']._serialized_start=8491
+  _globals['_ROLE']._serialized_end=8625
+  _globals['_VISIBILITY']._serialized_start=8627
+  _globals['_VISIBILITY']._serialized_end=8738
+  _globals['_HOOKACTION']._serialized_start=8741
+  _globals['_HOOKACTION']._serialized_end=8912
+  _globals['_CONTEXTINJECTIONROLE']._serialized_start=8915
+  _globals['_CONTEXTINJECTIONROLE']._serialized_end=9083
+  _globals['_APPROVALDEFAULT']._serialized_start=9085
+  _globals['_APPROVALDEFAULT']._serialized_end=9193
+  _globals['_USERMESSAGELEVEL']._serialized_start=9196
+  _globals['_USERMESSAGELEVEL']._serialized_end=9341
   _globals['_EMPTY']._serialized_start=44
   _globals['_EMPTY']._serialized_end=51
   _globals['_TOOLSPEC']._serialized_start=53
@@ -127,78 +127,80 @@
   _globals['_CHATRESPONSE']._serialized_end=4307
   _globals['_TOOLRESULT']._serialized_start=4309
   _globals['_TOOLRESULT']._serialized_end=4379
-  _globals['_HOOKRESULT']._serialized_start=4382
-  _globals['_HOOKRESULT']._serialized_end=4933
-  _globals['_MODELINFO']._serialized_start=4936
-  _globals['_MODELINFO']._serialized_end=5077
-  _globals['_PROVIDERINFO']._serialized_start=5080
-  _globals['_PROVIDERINFO']._serialized_end=5256
-  _globals['_APPROVALREQUEST']._serialized_start=5259
-  _globals['_APPROVALREQUEST']._serialized_end=5387
-  _globals['_APPROVALRESPONSE']._serialized_start=5389
-  _globals['_APPROVALRESPONSE']._serialized_end=5459
-  _globals['_LISTMODELSRESPONSE']._serialized_start=5461
-  _globals['_LISTMODELSRESPONSE']._serialized_end=5526
-  _globals['_PARSETOOLCALLSRESPONSE']._serialized_start=5528
-  _globals['_PARSETOOLCALLSRESPONSE']._serialized_end=5607
-  _globals['_ORCHESTRATOREXECUTEREQUEST']._serialized_start=5609
-  _globals['_ORCHESTRATOREXECUTEREQUEST']._serialized_end=5673
-  _globals['_ORCHESTRATOREXECUTERESPONSE']._serialized_start=5675
-  _globals['_ORCHESTRATOREXECUTERESPONSE']._serialized_end=5737
-  _globals['_ADDMESSAGEREQUEST']._serialized_start=5739
-  _globals['_ADDMESSAGEREQUEST']._serialized_end=5802
-  _globals['_GETMESSAGESRESPONSE']._serialized_start=5804
-  _globals['_GETMESSAGESRESPONSE']._serialized_end=5870
-  _globals['_GETMESSAGESFORREQUESTPARAMS']._serialized_start=5872
-  _globals['_GETMESSAGESFORREQUESTPARAMS']._serialized_end=5946
-  _globals['_SETMESSAGESREQUEST']._serialized_start=5948
-  _globals['_SETMESSAGESREQUEST']._serialized_end=6013
-  _globals['_HOOKHANDLEREQUEST']._serialized_start=6015
-  _globals['_HOOKHANDLEREQUEST']._serialized_end=6068
-  _globals['_GETSUBSCRIPTIONSREQUEST']._serialized_start=6070
-  _globals['_GETSUBSCRIPTIONSREQUEST']._serialized_end=6116
-  _globals['_GETSUBSCRIPTIONSRESPONSE']._serialized_start=6118
-  _globals['_GETSUBSCRIPTIONSRESPONSE']._serialized_end=6204
-  _globals['_EVENTSUBSCRIPTION']._serialized_start=6206
-  _globals['_EVENTSUBSCRIPTION']._serialized_end=6272
-  _globals['_COMPLETEWITHPROVIDERREQUEST']._serialized_start=6274
-  _globals['_COMPLETEWITHPROVIDERREQUEST']._serialized_end=6374
-  _globals['_EXECUTETOOLREQUEST']._serialized_start=6376
-  _globals['_EXECUTETOOLREQUEST']._serialized_end=6435
-  _globals['_EMITHOOKREQUEST']._serialized_start=6437
-  _globals['_EMITHOOKREQUEST']._serialized_end=6488
-  _globals['_EMITHOOKANDCOLLECTREQUEST']._serialized_start=6490
-  _globals['_EMITHOOKANDCOLLECTREQUEST']._serialized_end=6576
-  _globals['_EMITHOOKANDCOLLECTRESPONSE']._serialized_start=6578
-  _globals['_EMITHOOKANDCOLLECTRESPONSE']._serialized_end=6630
-  _globals['_GETMESSAGESREQUEST']._serialized_start=6632
-  _globals['_GETMESSAGESREQUEST']._serialized_end=6672
-  _globals['_KERNELADDMESSAGEREQUEST']._serialized_start=6674
-  _globals['_KERNELADDMESSAGEREQUEST']._serialized_end=6763
-  _globals['_GETMOUNTEDMODULEREQUEST']._serialized_start=6765
-  _globals['_GETMOUNTEDMODULEREQUEST']._serialized_end=6862
-  _globals['_GETMOUNTEDMODULERESPONSE']._serialized_start=6864
-  _globals['_GETMOUNTEDMODULERESPONSE']._serialized_end=6949
-  _globals['_REGISTERCAPABILITYREQUEST']._serialized_start=6951
-  _globals['_REGISTERCAPABILITYREQUEST']._serialized_end=7012
-  _globals['_GETCAPABILITYREQUEST']._serialized_start=7014
-  _globals['_GETCAPABILITYREQUEST']._serialized_end=7050
-  _globals['_GETCAPABILITYRESPONSE']._serialized_start=7052
-  _globals['_GETCAPABILITYRESPONSE']._serialized_end=7110
-  _globals['_TOOLSERVICE']._serialized_start=9099
-  _globals['_TOOLSERVICE']._serialized_end=9264
-  _globals['_PROVIDERSERVICE']._serialized_start=9267
-  _globals['_PROVIDERSERVICE']._serialized_end=9682
-  _globals['_ORCHESTRATORSERVICE']._serialized_start=9684
-  _globals['_ORCHESTRATORSERVICE']._serialized_end=9809
-  _globals['_CONTEXTSERVICE']._serialized_start=9812
-  _globals['_CONTEXTSERVICE']._serialized_end=10231
-  _globals['_HOOKSERVICE']._serialized_start=10234
-  _globals['_HOOKSERVICE']._serialized_end=10431
-  _globals['_APPROVALSERVICE']._serialized_start=10433
-  _globals['_APPROVALSERVICE']._serialized_end=10540
-  _globals['_KERNELSERVICE']._serialized_start=10543
-  _globals['_KERNELSERVICE']._serialized_end=11519
-  _globals['_MODULELIFECYCLE']._serialized_start=11522
-  _globals['_MODULELIFECYCLE']._serialized_end=11825
+  _globals['_CONTEXTINJECTION']._serialized_start=4382
+  _globals['_CONTEXTINJECTION']._serialized_end=4560
+  _globals['_HOOKRESULT']._serialized_start=4563
+  _globals['_HOOKRESULT']._serialized_end=5178
+  _globals['_MODELINFO']._serialized_start=5181
+  _globals['_MODELINFO']._serialized_end=5322
+  _globals['_PROVIDERINFO']._serialized_start=5325
+  _globals['_PROVIDERINFO']._serialized_end=5501
+  _globals['_APPROVALREQUEST']._serialized_start=5504
+  _globals['_APPROVALREQUEST']._serialized_end=5632
+  _globals['_APPROVALRESPONSE']._serialized_start=5634
+  _globals['_APPROVALRESPONSE']._serialized_end=5704
+  _globals['_LISTMODELSRESPONSE']._serialized_start=5706
+  _globals['_LISTMODELSRESPONSE']._serialized_end=5771
+  _globals['_PARSETOOLCALLSRESPONSE']._serialized_start=5773
+  _globals['_PARSETOOLCALLSRESPONSE']._serialized_end=5852
+  _globals['_ORCHESTRATOREXECUTEREQUEST']._serialized_start=5854
+  _globals['_ORCHESTRATOREXECUTEREQUEST']._serialized_end=5918
+  _globals['_ORCHESTRATOREXECUTERESPONSE']._serialized_start=5920
+  _globals['_ORCHESTRATOREXECUTERESPONSE']._serialized_end=5982
+  _globals['_ADDMESSAGEREQUEST']._serialized_start=5984
+  _globals['_ADDMESSAGEREQUEST']._serialized_end=6047
+  _globals['_GETMESSAGESRESPONSE']._serialized_start=6049
+  _globals['_GETMESSAGESRESPONSE']._serialized_end=6115
+  _globals['_GETMESSAGESFORREQUESTPARAMS']._serialized_start=6117
+  _globals['_GETMESSAGESFORREQUESTPARAMS']._serialized_end=6191
+  _globals['_SETMESSAGESREQUEST']._serialized_start=6193
+  _globals['_SETMESSAGESREQUEST']._serialized_end=6258
+  _globals['_HOOKHANDLEREQUEST']._serialized_start=6260
+  _globals['_HOOKHANDLEREQUEST']._serialized_end=6313
+  _globals['_GETSUBSCRIPTIONSREQUEST']._serialized_start=6315
+  _globals['_GETSUBSCRIPTIONSREQUEST']._serialized_end=6361
+  _globals['_GETSUBSCRIPTIONSRESPONSE']._serialized_start=6363
+  _globals['_GETSUBSCRIPTIONSRESPONSE']._serialized_end=6449
+  _globals['_EVENTSUBSCRIPTION']._serialized_start=6451
+  _globals['_EVENTSUBSCRIPTION']._serialized_end=6517
+  _globals['_COMPLETEWITHPROVIDERREQUEST']._serialized_start=6519
+  _globals['_COMPLETEWITHPROVIDERREQUEST']._serialized_end=6619
+  _globals['_EXECUTETOOLREQUEST']._serialized_start=6621
+  _globals['_EXECUTETOOLREQUEST']._serialized_end=6680
+  _globals['_EMITHOOKREQUEST']._serialized_start=6682
+  _globals['_EMITHOOKREQUEST']._serialized_end=6733
+  _globals['_EMITHOOKANDCOLLECTREQUEST']._serialized_start=6735
+  _globals['_EMITHOOKANDCOLLECTREQUEST']._serialized_end=6821
+  _globals['_EMITHOOKANDCOLLECTRESPONSE']._serialized_start=6823
+  _globals['_EMITHOOKANDCOLLECTRESPONSE']._serialized_end=6875
+  _globals['_GETMESSAGESREQUEST']._serialized_start=6877
+  _globals['_GETMESSAGESREQUEST']._serialized_end=6917
+  _globals['_KERNELADDMESSAGEREQUEST']._serialized_start=6919
+  _globals['_KERNELADDMESSAGEREQUEST']._serialized_end=7008
+  _globals['_GETMOUNTEDMODULEREQUEST']._serialized_start=7010
+  _globals['_GETMOUNTEDMODULEREQUEST']._serialized_end=7107
+  _globals['_GETMOUNTEDMODULERESPONSE']._serialized_start=7109
+  _globals['_GETMOUNTEDMODULERESPONSE']._serialized_end=7194
+  _globals['_REGISTERCAPABILITYREQUEST']._serialized_start=7196
+  _globals['_REGISTERCAPABILITYREQUEST']._serialized_end=7257
+  _globals['_GETCAPABILITYREQUEST']._serialized_start=7259
+  _globals['_GETCAPABILITYREQUEST']._serialized_end=7295
+  _globals['_GETCAPABILITYRESPONSE']._serialized_start=7297
+  _globals['_GETCAPABILITYRESPONSE']._serialized_end=7355
+  _globals['_TOOLSERVICE']._serialized_start=9344
+  _globals['_TOOLSERVICE']._serialized_end=9509
+  _globals['_PROVIDERSERVICE']._serialized_start=9512
+  _globals['_PROVIDERSERVICE']._serialized_end=9927
+  _globals['_ORCHESTRATORSERVICE']._serialized_start=9929
+  _globals['_ORCHESTRATORSERVICE']._serialized_end=10054
+  _globals['_CONTEXTSERVICE']._serialized_start=10057
+  _globals['_CONTEXTSERVICE']._serialized_end=10476
+  _globals['_HOOKSERVICE']._serialized_start=10479
+  _globals['_HOOKSERVICE']._serialized_end=10676
+  _globals['_APPROVALSERVICE']._serialized_start=10678
+  _globals['_APPROVALSERVICE']._serialized_end=10785
+  _globals['_KERNELSERVICE']._serialized_start=10788
+  _globals['_KERNELSERVICE']._serialized_end=11764
+  _globals['_MODULELIFECYCLE']._serialized_start=11767
+  _globals['_MODULELIFECYCLE']._serialized_end=12070
 # @@protoc_insertion_point(module_scope)
diff --git a/python/amplifier_core/hooks.py b/python/amplifier_core/hooks.py
index b8c8b79..c6e7492 100644
--- a/python/amplifier_core/hooks.py
+++ b/python/amplifier_core/hooks.py
@@ -1,5 +1,5 @@
 """Thin alias: re-exports RustHookRegistry (as HookRegistry) and HookResult."""
 from ._engine import RustHookRegistry as HookRegistry
-from .models import HookResult
+from .models import ContextInjection, HookResult
 
-__all__ = ["HookRegistry", "HookResult"]
+__all__ = ["HookRegistry", "ContextInjection", "HookResult"]
diff --git a/python/amplifier_core/loader_grpc.py b/python/amplifier_core/loader_grpc.py
index 41b0c3c..4759336 100644
--- a/python/amplifier_core/loader_grpc.py
+++ b/python/amplifier_core/loader_grpc.py
@@ -195,8 +195,7 @@ async def load_grpc_module(
     except ImportError:
         raise ImportError(
             "gRPC proto stubs not generated. Run: "
-            "python -m grpc_tools.protoc -I proto --python_out=python/amplifier_core/_grpc_gen "
-            "--grpc_python_out=python/amplifier_core/_grpc_gen proto/amplifier_module.proto"
+            "python scripts/generate_grpc_stubs.py"
         )
 
     stub = amplifier_module_pb2_grpc.ToolServiceStub(channel)
diff --git a/python/amplifier_core/models.py b/python/amplifier_core/models.py
index 2bf3330..be568f1 100644
--- a/python/amplifier_core/models.py
+++ b/python/amplifier_core/models.py
@@ -124,6 +124,17 @@ def get_serialized_output(self) -> str:
         return "Success"
 
 
+class ContextInjection(BaseModel):
+    """One ordered context injection emitted by a hook."""
+
+    content: str
+    role: Literal["system", "user", "assistant"] = "system"
+    ephemeral: bool = False
+    append_to_last_tool_result: bool = False
+    hook_name: str = "unknown"
+    event: str = ""
+
+
 class HookResult(BaseModel):
     """
     Result from hook execution with enhanced capabilities.
@@ -323,6 +334,13 @@ class HookResult(BaseModel):
             "Only applicable when action='inject_context' and ephemeral=True."
         ),
     )
+    context_injections: list[ContextInjection] = Field(
+        default_factory=list,
+        description=(
+            "Ordered, lossless hook context injections. The hook registry projects "
+            "the legacy scalar context fields from these items for compatibility."
+        ),
+    )
 
 
 class ModelInfo(BaseModel):
diff --git a/scripts/generate_grpc_stubs.py b/scripts/generate_grpc_stubs.py
new file mode 100644
index 0000000..11ad49e
--- /dev/null
+++ b/scripts/generate_grpc_stubs.py
@@ -0,0 +1,63 @@
+#!/usr/bin/env python3
+"""Generate package-safe Python gRPC stubs from the canonical proto."""
+
+from __future__ import annotations
+
+import argparse
+from importlib.metadata import version
+import subprocess
+import sys
+from pathlib import Path
+
+
+PROJECT_ROOT = Path(__file__).resolve().parent.parent
+PROTO_PATH = PROJECT_ROOT / "proto" / "amplifier_module.proto"
+RAW_IMPORT = "import amplifier_module_pb2 as amplifier__module__pb2"
+PACKAGE_IMPORT = "from . import amplifier_module_pb2 as amplifier__module__pb2"
+GRPCIO_TOOLS_VERSION = "1.78.0"
+
+
+def main() -> None:
+    if version("grpcio-tools") != GRPCIO_TOOLS_VERSION:
+        raise RuntimeError(
+            f"grpcio-tools=={GRPCIO_TOOLS_VERSION} is required; install it with "
+            f"`python -m pip install grpcio-tools=={GRPCIO_TOOLS_VERSION}`."
+        )
+    parser = argparse.ArgumentParser(
+        description="Generate package-safe Python stubs for amplifier_module.proto."
+    )
+    parser.add_argument(
+        "--output",
+        type=Path,
+        default=Path("python/amplifier_core/_grpc_gen"),
+        help="Output directory, relative to the repository root by default.",
+    )
+    args = parser.parse_args()
+    output = args.output if args.output.is_absolute() else PROJECT_ROOT / args.output
+    output.mkdir(parents=True, exist_ok=True)
+
+    subprocess.run(
+        [
+            sys.executable,
+            "-m",
+            "grpc_tools.protoc",
+            "-Iproto",
+            f"--python_out={output}",
+            f"--grpc_python_out={output}",
+            str(PROTO_PATH.relative_to(PROJECT_ROOT)),
+        ],
+        cwd=PROJECT_ROOT,
+        check=True,
+    )
+
+    grpc_stub = output / "amplifier_module_pb2_grpc.py"
+    generated = grpc_stub.read_text()
+    if RAW_IMPORT not in generated:
+        raise RuntimeError(
+            f"Expected generated import not found in {grpc_stub}: {RAW_IMPORT!r}"
+        )
+    grpc_stub.write_text(generated.replace(RAW_IMPORT, PACKAGE_IMPORT, 1))
+
+
+if __name__ == "__main__":
+    main()
\ No newline at end of file
diff --git a/tests/test_generated_equivalence.py b/tests/test_generated_equivalence.py
index 18e643e..42ff9f4 100644
--- a/tests/test_generated_equivalence.py
+++ b/tests/test_generated_equivalence.py
@@ -32,7 +32,7 @@ def test_proto_tool_result_field_count(self):
 
 
 class TestHookResultEquivalence:
-    """Proto HookResult has all 15 fields matching native HookResult."""
+    """Proto HookResult has all 16 fields matching native HookResult."""
 
     def test_proto_hook_result_has_all_fields(self):
         hr = pb2.HookResult()
@@ -52,15 +52,37 @@ def test_proto_hook_result_has_all_fields(self):
             "user_message_level",
             "user_message_source",
             "append_to_last_tool_result",
+            "context_injections",
         ]
-        for field in expected_fields:
-            assert hasattr(hr, field), f"HookResult missing field: {field}"
+        assert [field.name for field in hr.DESCRIPTOR.fields] == expected_fields
 
     def test_proto_hook_result_field_count(self):
-        """HookResult must have exactly 15 fields."""
+        """HookResult must have exactly 16 append-only fields."""
         hr = pb2.HookResult()
-        fields = [f.name for f in hr.DESCRIPTOR.fields]
-        assert len(fields) == 15, f"Expected 15 fields, got {len(fields)}: {fields}"
+        expected_numbers = {
+            "action": 1,
+            "data_json": 2,
+            "reason": 3,
+            "context_injection": 4,
+            "context_injection_role": 5,
+            "ephemeral": 6,
+            "approval_prompt": 7,
+            "approval_options": 8,
+            "approval_timeout": 9,
+            "approval_default": 10,
+            "suppress_output": 11,
+            "user_message": 12,
+            "user_message_level": 13,
+            "user_message_source": 14,
+            "append_to_last_tool_result": 15,
+            "context_injections": 16,
+        }
+        assert {field.name: field.number for field in hr.DESCRIPTOR.fields} == expected_numbers
+
+        injections = hr.DESCRIPTOR.fields_by_name["context_injections"]
+        assert injections.is_repeated
+        assert injections.type == injections.TYPE_MESSAGE
+        assert injections.message_type.full_name == pb2.ContextInjection.DESCRIPTOR.full_name
 
 
 class TestHookActionEnumEquivalence:
diff --git a/tests/test_hooks_alias.py b/tests/test_hooks_alias.py
index 29449f5..1133a5a 100644
--- a/tests/test_hooks_alias.py
+++ b/tests/test_hooks_alias.py
@@ -3,7 +3,8 @@
 """
 
 import amplifier_core.hooks as hooks_module
-from amplifier_core.hooks import HookRegistry, HookResult
+from amplifier_core.hooks import ContextInjection, HookRegistry, HookResult
+from amplifier_core.models import ContextInjection as ModelContextInjection
 
 
 def test_import_hook_registry():
@@ -37,7 +38,8 @@ def test_hook_registry_instantiation():
 
 
 def test_all_exports():
-    """__all__ contains exactly HookRegistry and HookResult."""
+    """__all__ exposes every public hook result type."""
     all_exports = getattr(hooks_module, "__all__", None)
     assert all_exports is not None, "hooks module should define __all__"
-    assert set(all_exports) == {"HookRegistry", "HookResult"}
+    assert set(all_exports) == {"HookRegistry", "ContextInjection", "HookResult"}
+    assert ContextInjection is ModelContextInjection
diff --git a/tests/test_hooks_request_id.py b/tests/test_hooks_request_id.py
index 89657a2..c85885f 100644
--- a/tests/test_hooks_request_id.py
+++ b/tests/test_hooks_request_id.py
@@ -209,45 +209,77 @@ async def test_emit_carries_request_id_onto_the_error_path():
 async def test_concurrent_calls_get_distinct_ids_and_pair_correctly():
     """The case FIFO gets wrong.
 
-    Interleaving is forced to reproduce the measured trace (agent request,
-    summarizer request, summarizer response, agent response) where positional
-    pairing charges each response to the other caller.
+    Both request callbacks enter and suspend before either can resume. This
+    deterministically proves concurrent in-flight calls without relying on
+    task scheduling order.
     """
     registry = HookRegistry()
     seen = []
-    for event in ("llm:request", "llm:response"):
-        registry.register(event, _recorder(seen), name=f"cap-{event}")
+    request_ids_before_await = {}
+    request_ids_after_await = {}
+    callback_trace = []
+    all_request_callbacks_entered = asyncio.Event()
+    release_request_callbacks = asyncio.Event()
+
+    async def capture(event, data):
+        payload = dict(data)
+        caller = payload["caller"]
+        if event == "llm:request":
+            request_ids_before_await[caller] = payload[REQUEST_ID_FIELD]
+            callback_trace.append(("request-start", caller))
+            if len(request_ids_before_await) == 2:
+                all_request_callbacks_entered.set()
+            await release_request_callbacks.wait()
+            request_ids_after_await[caller] = payload[REQUEST_ID_FIELD]
+            callback_trace.append(("request-end", caller))
+        seen.append((event, payload))
+        return HookResult(action="continue")
 
-    summarizer_requested = asyncio.Event()
-    summarizer_responded = asyncio.Event()
+    for event in ("llm:request", "llm:response"):
+        registry.register(event, capture, name=f"cap-{event}")
 
     async def agent_call():
         await registry.emit("llm:request", {"caller": "agent"})
-        await summarizer_responded.wait()
         await registry.emit("llm:response", {"caller": "agent"})
 
     async def summarizer_call():
-        await summarizer_requested.wait()
         await registry.emit("llm:request", {"caller": "summarizer"})
         await registry.emit("llm:response", {"caller": "summarizer"})
-        summarizer_responded.set()
 
     async def run():
         task_agent = asyncio.create_task(agent_call())
         task_summarizer = asyncio.create_task(summarizer_call())
-        await asyncio.sleep(0)
-        summarizer_requested.set()
-        await asyncio.gather(task_agent, task_summarizer)
+        try:
+            await asyncio.wait_for(all_request_callbacks_entered.wait(), timeout=10)
+        except TimeoutError:
+            release_request_callbacks.set()
+            await asyncio.gather(task_agent, task_summarizer, return_exceptions=True)
+            pytest.fail(
+                "Concurrent emits did not enter both request callbacks before either resumed"
+            )
+        release_request_callbacks.set()
+        try:
+            await asyncio.wait_for(
+                asyncio.gather(task_agent, task_summarizer),
+                timeout=10,
+            )
+        except TimeoutError:
+            pytest.fail("Concurrent emits did not complete after callbacks were released")
 
     await run()
 
-    order = [(event, payload["caller"]) for event, payload in seen]
-    assert order == [
-        ("llm:request", "agent"),
-        ("llm:request", "summarizer"),
-        ("llm:response", "summarizer"),
-        ("llm:response", "agent"),
-    ], "expected the interleaving that defeats positional pairing"
+    assert {caller for phase, caller in callback_trace if phase == "request-start"} == {
+        "agent",
+        "summarizer",
+    }
+    first_end = next(
+        index
+        for index, (phase, _) in enumerate(callback_trace)
+        if phase == "request-end"
+    )
+    assert all(phase == "request-start" for phase, _ in callback_trace[:first_end])
+    assert set(request_ids_before_await) == {"agent", "summarizer"}
+    assert request_ids_before_await == request_ids_after_await
 
     by_caller = {}
     for event, payload in seen:
@@ -260,13 +292,6 @@ async def run():
     assert summarizer["llm:request"] == summarizer["llm:response"]
     assert agent["llm:request"] != summarizer["llm:request"]
 
-    # And the positional pairing this replaces would have crossed them:
-    # FIFO joins the first request to the first response, which here belong
-    # to different callers.
-    requests = [p[REQUEST_ID_FIELD] for e, p in seen if e == "llm:request"]
-    responses = [p[REQUEST_ID_FIELD] for e, p in seen if e == "llm:response"]
-    assert requests[0] != responses[0], "expected FIFO to mis-pair this trace"
-
 
 @pytest.mark.asyncio
 async def test_many_concurrent_calls_all_pair_correctly():
diff --git a/tests/test_injection_items.py b/tests/test_injection_items.py
new file mode 100644
index 0000000..604d629
--- /dev/null
+++ b/tests/test_injection_items.py
@@ -0,0 +1,20 @@
+"""Regression coverage for lossless mixed hook context injections."""
+
+from amplifier_core.models import ContextInjection, HookResult
+
+
+def test_mixed_durable_and_ephemeral_injections_remain_distinct() -> None:
+    result = HookResult(
+        action="inject_context",
+        context_injections=[
+            ContextInjection(content="durable", role="assistant", ephemeral=False),
+            ContextInjection(content="temporary", role="user", ephemeral=True),
+        ],
+    )
+
+    assert [item.content for item in result.context_injections] == [
+        "durable",
+        "temporary",
+    ]
+    assert [item.ephemeral for item in result.context_injections] == [False, True]
+    assert [item.role for item in result.context_injections] == ["assistant", "user"]
\ No newline at end of file
diff --git a/tests/test_proto_compilation.py b/tests/test_proto_compilation.py
index 9a0084e..db8bfdc 100644
--- a/tests/test_proto_compilation.py
+++ b/tests/test_proto_compilation.py
@@ -4,6 +4,16 @@
 service messages, all 8 gRPC service stubs, and enum value assignments.
 """
 
+import shutil
+import subprocess
+import sys
+from pathlib import Path
+
+
+GRPC_GEN_DIR = (
+    Path(__file__).parent.parent / "python" / "amplifier_core" / "_grpc_gen"
+)
+
 
 class TestProtoCompilation:
     """Verify proto-generated modules import cleanly and expose expected symbols."""
@@ -16,6 +26,26 @@ def test_pb2_grpc_module_imports(self):
         """The pb2_grpc module imports without error."""
         from amplifier_core._grpc_gen import amplifier_module_pb2_grpc  # noqa: F401
 
+    def test_pb2_grpc_imports_as_a_package(self, tmp_path):
+        """The stub resolves its sibling pb2 module without a flat module path."""
+        package_root = tmp_path / "isolated_package"
+        package_root.mkdir()
+        (package_root / "__init__.py").touch()
+        shutil.copytree(GRPC_GEN_DIR, package_root / "_grpc_gen")
+
+        result = subprocess.run(
+            [
+                sys.executable,
+                "-c",
+                "from isolated_package._grpc_gen import amplifier_module_pb2_grpc",
+            ],
+            cwd=tmp_path,
+            capture_output=True,
+            text=True,
+        )
+
+        assert result.returncode == 0, result.stderr
+
     def test_tool_service_messages_exist(self):
         """Backward-compat: original ToolService messages are present."""
         from amplifier_core._grpc_gen import amplifier_module_pb2 as pb2