diff --git a/packages/ai-service/Dockerfile b/packages/ai-service/Dockerfile
index 5be8676..56c2d6c 100644
--- a/packages/ai-service/Dockerfile
+++ b/packages/ai-service/Dockerfile
@@ -1,5 +1,5 @@
 # ---- Build Stage ----
-FROM mcr.microsoft.com/cbl-mariner/base/python:3.12 AS builder
+FROM mcr.microsoft.com/azurelinux/base/python:3.12 AS builder
 WORKDIR /app
 
 COPY packages/ai-service/requirements.txt .
@@ -11,13 +11,15 @@ RUN pip install --no-cache-dir \
       --target=/deps -r requirements.txt
 
 # ---- Production Stage ----
-FROM mcr.microsoft.com/cbl-mariner/base/python:3.12 AS production
+FROM mcr.microsoft.com/azurelinux/base/python:3.12 AS production
 WORKDIR /app
 
+# wget for the HEALTHCHECK; shadow-utils provides groupadd/useradd (not in the base image)
+RUN tdnf install -y wget shadow-utils && tdnf clean all
 RUN groupadd -r agentbase && useradd -r -g agentbase -s /sbin/nologin -M agentbase
-RUN tdnf install -y wget
 
-COPY --from=builder /deps /usr/local/lib/python3.12/site-packages
+# Azure Linux's system interpreter resolves /usr/lib/python3.12/site-packages on sys.path
+COPY --from=builder /deps /usr/lib/python3.12/site-packages
 COPY packages/ai-service/app ./app
 
 USER agentbase
diff --git a/packages/core/Dockerfile b/packages/core/Dockerfile
index 77b4858..b43a6a4 100644
--- a/packages/core/Dockerfile
+++ b/packages/core/Dockerfile
@@ -1,5 +1,5 @@
 # ---- Build Stage ----
-FROM mcr.microsoft.com/cbl-mariner/base/nodejs:20 AS builder
+FROM mcr.microsoft.com/azurelinux/base/nodejs:20 AS builder
 WORKDIR /app
 
 # Install pnpm
@@ -28,11 +28,12 @@ WORKDIR /app/packages/core
 RUN npx nest build
 
 # ---- Production Stage ----
-FROM mcr.microsoft.com/cbl-mariner/base/nodejs:20 AS production
+FROM mcr.microsoft.com/azurelinux/base/nodejs:20 AS production
 WORKDIR /app
 
 RUN corepack enable && corepack prepare pnpm@9 --activate
-RUN tdnf install -y wget
+# wget for the HEALTHCHECK; shadow-utils provides groupadd/useradd (not in the base image)
+RUN tdnf install -y wget shadow-utils && tdnf clean all
 
 # Copy built app
 COPY --from=builder /app/packages/core/dist ./dist
diff --git a/packages/frontend/Dockerfile b/packages/frontend/Dockerfile
index 25b9f07..6da6fc0 100644
--- a/packages/frontend/Dockerfile
+++ b/packages/frontend/Dockerfile
@@ -1,5 +1,5 @@
 # ---- Build Stage ----
-FROM mcr.microsoft.com/cbl-mariner/base/nodejs:20 AS builder
+FROM mcr.microsoft.com/azurelinux/base/nodejs:20 AS builder
 WORKDIR /app
 
 RUN corepack enable && corepack prepare pnpm@9 --activate
@@ -30,10 +30,11 @@ ENV NEXT_PUBLIC_AI_URL=$NEXT_PUBLIC_AI_URL
 RUN npx next build
 
 # ---- Production Stage ----
-FROM mcr.microsoft.com/cbl-mariner/base/nodejs:20 AS production
+FROM mcr.microsoft.com/azurelinux/base/nodejs:20 AS production
 WORKDIR /app
 
-RUN tdnf install -y wget
+# wget for the HEALTHCHECK; shadow-utils provides groupadd/useradd (not in the base image)
+RUN tdnf install -y wget shadow-utils && tdnf clean all
 
 COPY --from=builder /app/packages/frontend/.next/standalone ./
 COPY --from=builder /app/packages/frontend/.next/static ./.next/static