diff --git a/skaffold.yaml b/skaffold.yaml
index 9a13f5f2ee7..0bdc565de21 100644
--- a/skaffold.yaml
+++ b/skaffold.yaml
@@ -41,8 +41,6 @@ build:
     context: src/currencyservice
   - image: cartservice
     context: src/cartservice/src
-    docker:
-      dockerfile: Dockerfile
   - image: frontend
     context: src/frontend
   - image: adservice
@@ -81,9 +79,20 @@ profiles:
   activation:
   - command: debug
   patches:
-  - op: replace
-    path: /build/artifacts/7/docker/dockerfile
-    value: Dockerfile.debug
+  - op: add
+    path: /build/artifacts/0/docker
+    value:
+      buildArgs:
+        SKAFFOLD_PY_DEBUG: "true"
+  - op: add
+    path: /build/artifacts/2/docker
+    value:
+      buildArgs:
+        SKAFFOLD_PY_DEBUG: "true"
+  - op: add
+    path: /build/artifacts/8/docker
+    value:
+      dockerfile: Dockerfile.debug
 # The "network-policies" profile is not used by default.
 # You can use it in isolation or in combination with other profiles:
 #     skaffold run -p network-policies, debug
@@ -120,3 +129,12 @@ profiles:
       diskSizeGb: 300
       machineType: N1_HIGHCPU_32
       timeout: 4000s
+- name: debug
+  activation:
+    - command: debug
+  patches:
+  - op: add
+    path: /build/artifacts/0/docker
+    value:
+      buildArgs:
+        SKAFFOLD_PY_DEBUG: "true"
diff --git a/src/cartservice/src/Dockerfile.debug b/src/cartservice/src/Dockerfile.debug
index 1c24ac95847..0f4d878b8ca 100644
--- a/src/cartservice/src/Dockerfile.debug
+++ b/src/cartservice/src/Dockerfile.debug
@@ -12,7 +12,7 @@
 # See the License for the specific language governing permissions and
 # limitations under the License.
 
-FROM mcr.microsoft.com/dotnet/sdk:10.0@sha256:d599d654aa6fd7baabe54b4272dc475768307ef4d8a07d6e9f9b50b7b1758059 AS build
+FROM mcr.microsoft.com/dotnet/sdk:9.0@sha256:7d24e90a392e88eb56093e4eb325ff883ad609382a55d42f17fd557b997022ca AS build
 WORKDIR /app
 COPY . .
 RUN dotnet restore cartservice.csproj
@@ -22,7 +22,7 @@ FROM build AS publish
 RUN dotnet publish cartservice.csproj -c Debug -o /out
 
 # Building final image used in running container
-FROM mcr.microsoft.com/dotnet/aspnet:10.0@sha256:5b558c0d5f65031e34528f0c68c954f03f4db77ee18504cad183d239328f55ca AS final
+FROM mcr.microsoft.com/dotnet/aspnet:9.0@sha256:372b16214ae67e3626a5b1513ade4a530eae10c172d56ce696163b046565fa46 AS final
 # Installing procps on the container to enable debugging of .NET Core
 RUN apt-get update \
     && apt-get install -y unzip procps wget
diff --git a/src/emailservice/Dockerfile b/src/emailservice/Dockerfile
index 47688ab0ad3..14d36455eaa 100644
--- a/src/emailservice/Dockerfile
+++ b/src/emailservice/Dockerfile
@@ -24,6 +24,11 @@ RUN apk update \
 COPY requirements.txt .
 RUN pip install -r requirements.txt
 
+ARG SKAFFOLD_PY_DEBUG=false
+RUN if [ "$SKAFFOLD_PY_DEBUG" = "true" ]; then \
+      pip install debugpy; \
+    fi
+
 FROM base
 # Enable unbuffered logging
 ENV PYTHONUNBUFFERED=1
diff --git a/src/loadgenerator/Dockerfile b/src/loadgenerator/Dockerfile
index f7a201eb42f..ca912bafa71 100644
--- a/src/loadgenerator/Dockerfile
+++ b/src/loadgenerator/Dockerfile
@@ -24,6 +24,11 @@ COPY requirements.txt .
 
 RUN pip install --prefix="/install" -r requirements.txt
 
+ARG SKAFFOLD_PY_DEBUG=false
+RUN if [ "$SKAFFOLD_PY_DEBUG" = "true" ]; then \
+      pip install --prefix="/install" debugpy; \
+    fi
+
 FROM base
 
 RUN apk update \
diff --git a/src/recommendationservice/Dockerfile b/src/recommendationservice/Dockerfile
index bfda525572a..bae56d1d02a 100644
--- a/src/recommendationservice/Dockerfile
+++ b/src/recommendationservice/Dockerfile
@@ -24,6 +24,11 @@ RUN apk update \
 COPY requirements.txt .
 RUN pip install -r requirements.txt
 
+ARG SKAFFOLD_PY_DEBUG=false
+RUN if [ "$SKAFFOLD_PY_DEBUG" = "true" ]; then \
+      pip install debugpy; \
+    fi
+
 FROM base
 # Enable unbuffered logging
 ENV PYTHONUNBUFFERED=1