diff --git a/dandi/cli/base.py b/dandi/cli/base.py
index 9d8bc6ace..1b118d7ed 100644
--- a/dandi/cli/base.py
+++ b/dandi/cli/base.py
@@ -1,3 +1,4 @@
+from enum import Enum
 from functools import wraps
 import os
 
@@ -29,6 +30,24 @@ def get_metavar(self, param, ctx=None):
         return "N[:M]"
 
 
+class EnumChoice(click.Choice):
+    """A ``click.Choice`` over a ``str``-valued ``Enum``, matched on member values.
+
+    The available choices presented on the command line are the enum member
+    values (e.g. ``error``, ``skip``), and ``convert`` returns the corresponding
+    enum member. A string default is converted to its member as well.
+    """
+
+    def __init__(self, enum_cls: type[Enum], case_sensitive: bool = True) -> None:
+        self.enum_cls = enum_cls
+        super().__init__([e.value for e in enum_cls], case_sensitive=case_sensitive)
+
+    def convert(self, value, param, ctx):
+        if value is None or isinstance(value, self.enum_cls):
+            return value
+        return self.enum_cls(super().convert(value, param, ctx))
+
+
 class ChoiceList(click.ParamType):
     name = "choice-list"
 
diff --git a/dandi/cli/cmd_download.py b/dandi/cli/cmd_download.py
index 4547ae043..7dee42cc4 100644
--- a/dandi/cli/cmd_download.py
+++ b/dandi/cli/cmd_download.py
@@ -5,7 +5,13 @@
 
 import click
 
-from .base import ChoiceList, IntColonInt, instance_option, map_to_click_exceptions
+from .base import (
+    ChoiceList,
+    EnumChoice,
+    IntColonInt,
+    instance_option,
+    map_to_click_exceptions,
+)
 from ..consts import SyncMode
 from ..dandiarchive import _dandi_url_parser, parse_dandi_url
 from ..dandiset import Dandiset
@@ -63,7 +69,7 @@
 @click.option(
     "-e",
     "--existing",
-    type=click.Choice(list(DownloadExisting)),
+    type=EnumChoice(DownloadExisting),
     # TODO: verify-reupload (to become default)
     help="How to handle paths that already exist locally. "
     "For 'error', if the local file exists, display an error and skip downloading that asset. "
@@ -80,12 +86,12 @@
     "-f",
     "--format",
     help="Choose the format/frontend for output. TODO: support all of the ls",
-    type=click.Choice(list(DownloadFormat)),
+    type=EnumChoice(DownloadFormat),
     default="pyout",
 )
 @click.option(
     "--path-type",
-    type=click.Choice(list(PathType)),
+    type=EnumChoice(PathType),
     default="exact",
     help="Whether to interpret asset paths in URLs as exact matches or glob patterns",
     show_default=True,
@@ -121,7 +127,7 @@
     is_flag=False,
     flag_value="ask",
     default=None,
-    type=click.Choice(list(SyncMode)),
+    type=EnumChoice(SyncMode),
     help="Delete local assets that do not exist on the server. "
     "With 'ask' (the default when --sync is passed without a value), prompt before "
     "deleting. With 'do', delete without prompting.",
diff --git a/dandi/cli/cmd_move.py b/dandi/cli/cmd_move.py
index 6a8898f9a..ebc3e42d2 100644
--- a/dandi/cli/cmd_move.py
+++ b/dandi/cli/cmd_move.py
@@ -2,7 +2,12 @@
 
 import click
 
-from .base import devel_debug_option, instance_option, map_to_click_exceptions
+from .base import (
+    EnumChoice,
+    devel_debug_option,
+    instance_option,
+    map_to_click_exceptions,
+)
 from ..move import MoveExisting, MoveWorkOn
 
 
@@ -16,7 +21,7 @@
 @click.option(
     "-e",
     "--existing",
-    type=click.Choice(list(MoveExisting)),
+    type=EnumChoice(MoveExisting),
     default="error",
     help="How to handle assets that would be moved to a destination that already exists",
     show_default=True,
@@ -30,7 +35,7 @@
 @click.option(
     "-w",
     "--work-on",
-    type=click.Choice(list(MoveWorkOn)),
+    type=EnumChoice(MoveWorkOn),
     default="auto",
     help=(
         "Whether to operate on the local Dandiset, remote Dandiset, or both;"
diff --git a/dandi/cli/cmd_organize.py b/dandi/cli/cmd_organize.py
index f5c1e216c..47930cbab 100644
--- a/dandi/cli/cmd_organize.py
+++ b/dandi/cli/cmd_organize.py
@@ -2,7 +2,12 @@
 
 import click
 
-from .base import dandiset_path_option, devel_debug_option, map_to_click_exceptions
+from .base import (
+    EnumChoice,
+    dandiset_path_option,
+    devel_debug_option,
+    map_to_click_exceptions,
+)
 from ..consts import dandi_layout_fields
 from ..organize import CopyMode, FileOperationMode, OrganizeInvalid
 
@@ -17,7 +22,7 @@
 @click.option(
     "--invalid",
     help="What to do if files without sufficient metadata are encountered.",
-    type=click.Choice(list(OrganizeInvalid)),
+    type=EnumChoice(OrganizeInvalid),
     default="fail",
     show_default=True,
 )
@@ -30,7 +35,7 @@
     "If 'auto' - whichever of symlink, hardlink, copy is allowed by system. "
     "The other modes (copy, move, symlink, hardlink) define how data files "
     "should be made available.",
-    type=click.Choice(list(FileOperationMode)),
+    type=EnumChoice(FileOperationMode),
     default="auto",
     show_default=True,
 )
@@ -45,7 +50,7 @@
 )
 @click.option(
     "--media-files-mode",
-    type=click.Choice(list(CopyMode)),
+    type=EnumChoice(CopyMode),
     default=None,
     help="How to relocate video files referenced by NWB files",
 )
diff --git a/dandi/cli/cmd_upload.py b/dandi/cli/cmd_upload.py
index 25222a38e..9b5f1760c 100644
--- a/dandi/cli/cmd_upload.py
+++ b/dandi/cli/cmd_upload.py
@@ -3,6 +3,7 @@
 import click
 
 from .base import (
+    EnumChoice,
     IntColonInt,
     devel_debug_option,
     devel_option,
@@ -17,7 +18,7 @@
 @click.option(
     "-e",
     "--existing",
-    type=click.Choice(list(UploadExisting)),
+    type=EnumChoice(UploadExisting),
     help="What to do if a file found existing on the server. 'skip' would skip"
     "the file, 'force' - force reupload, 'overwrite' - force upload if "
     "either size or modification time differs; 'refresh' - upload only if "
@@ -40,7 +41,7 @@
     is_flag=False,
     flag_value="ask",
     default=None,
-    type=click.Choice(list(SyncMode)),
+    type=EnumChoice(SyncMode),
     help="Delete assets on the server that do not exist locally. "
     "With 'ask' (the default when --sync is passed without a value), prompt before "
     "deleting. With 'do', delete without prompting.",
@@ -52,7 +53,7 @@
     "'require' - data must pass validation before upload; "
     "'skip' - no validation is performed on data before upload; "
     "'ignore' - data is validated but upload proceeds regardless of validation results.",
-    type=click.Choice(list(UploadValidation)),
+    type=EnumChoice(UploadValidation),
     default="require",
     show_default=True,
 )
diff --git a/dandi/cli/tests/test_base.py b/dandi/cli/tests/test_base.py
new file mode 100644
index 000000000..1576f422a
--- /dev/null
+++ b/dandi/cli/tests/test_base.py
@@ -0,0 +1,74 @@
+from enum import Enum
+
+import click
+from click.testing import CliRunner
+import pytest
+
+from ..base import EnumChoice
+
+
+class _Existing(str, Enum):
+    ERROR = "error"
+    SKIP = "skip"
+    OVERWRITE = "overwrite-different"
+
+    def __str__(self) -> str:
+        return self.value
+
+
+def _make_command(**option_kwargs):
+    @click.command()
+    @click.option("--existing", type=EnumChoice(_Existing), **option_kwargs)
+    def cmd(existing):
+        click.echo(f"{type(existing).__name__}:{existing!r}")
+
+    return cmd
+
+
+@pytest.mark.ai_generated
+def test_enum_choice_accepts_member_value():
+    captured = {}
+
+    @click.command()
+    @click.option("--existing", type=EnumChoice(_Existing), default="error")
+    def cmd(existing):
+        captured["existing"] = existing
+
+    r = CliRunner().invoke(cmd, ["--existing", "overwrite-different"])
+    assert r.exit_code == 0, r.output
+    assert captured["existing"] is _Existing.OVERWRITE
+
+
+@pytest.mark.ai_generated
+def test_enum_choice_rejects_member_name():
+    r = CliRunner().invoke(_make_command(default="error"), ["--existing", "SKIP"])
+    assert r.exit_code != 0
+    assert "'SKIP' is not one of" in r.output
+
+
+@pytest.mark.ai_generated
+def test_enum_choice_none_default_passes_through():
+    captured = {}
+
+    @click.command()
+    @click.option("--existing", type=EnumChoice(_Existing), default=None)
+    def cmd(existing):
+        captured["existing"] = existing
+
+    r = CliRunner().invoke(cmd, [])
+    assert r.exit_code == 0, r.output
+    assert captured["existing"] is None
+
+
+@pytest.mark.ai_generated
+def test_enum_choice_string_default_converted_to_member():
+    captured = {}
+
+    @click.command()
+    @click.option("--existing", type=EnumChoice(_Existing), default="skip")
+    def cmd(existing):
+        captured["existing"] = existing
+
+    r = CliRunner().invoke(cmd, [])
+    assert r.exit_code == 0, r.output
+    assert captured["existing"] is _Existing.SKIP
diff --git a/pyproject.toml b/pyproject.toml
index 7454bb12f..a7623e51c 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -46,8 +46,7 @@ classifiers = [
 dependencies = [
     "bidsschematools ~= 1.0",
     "bids-validator-deno >= 2.0.5",
-    # >=8.2.0: https://github.com/pallets/click/issues/2911
-    "click >= 7.1, <8.2.0",
+    "click >= 7.1",
     "click-didyoumean",
     "dandischema ~= 0.12.0",
     "etelemetry >= 0.2.2",