diff --git a/application/single_app/Dockerfile b/application/single_app/Dockerfile
index 65483ac6..57f377ee 100644
--- a/application/single_app/Dockerfile
+++ b/application/single_app/Dockerfile
@@ -7,15 +7,13 @@ FROM mcr.microsoft.com/azurelinux/base/python:3.12 AS builder
 ARG UID
 ARG GID
 
-# Setup pip.conf if has content
-COPY pip.conf.d/ /etc/pip.conf.d
+# Copy pip.conf into the image for pip configuration
+COPY docker-customization/pip.conf /etc/pip.conf
 
 # CA
 # copy certs to /etc/pki/ca-trust/source/anchors
-COPY custom-ca-certificates/ /etc/ssl/certs
-RUN mkdir -p /etc/pki/ca-trust/source/anchors/ \
-    && update-ca-trust enable \
-    && cp /etc/ssl/certs/*.crt /etc/pki/ca-trust/source/anchors/ \
+COPY docker-customization/custom-ca-certificates/ /etc/pki/ca-trust/source/anchors
+RUN update-ca-trust enable \
     && update-ca-trust extract
 
 ENV PYTHONUNBUFFERED=1
@@ -44,6 +42,7 @@ ARG UID
 ARG GID
 
 COPY --from=builder /etc/pki /etc/pki
+COPY --from=builder /etc/ssl/certs /etc/ssl/certs
 COPY --from=builder /home/nonroot /home/nonroot
 COPY --from=builder /etc/passwd /etc/passwd
 COPY --from=builder /etc/group /etc/group
@@ -59,8 +58,11 @@ ENV HOME=/home/nonroot \
     PYTHONIOENCODING=utf-8 \
     LANG=C.UTF-8 \
     LC_ALL=C.UTF-8 \
-    PYTHONUNBUFFERED=1
-
+    PYTHONUNBUFFERED=1 \
+    SSL_CERT_FILE=/etc/ssl/certs/ca-bundle.crt \
+    SSL_CERT_DIR=/etc/ssl/certs \
+    REQUESTS_CA_BUNDLE=/etc/ssl/certs/ca-bundle.crt
+    
 WORKDIR /app
 
 # Copy application code and set ownership
diff --git a/custom-ca-certificates/.gitkeep b/docker-customization/custom-ca-certificates/.gitkeep
similarity index 100%
rename from custom-ca-certificates/.gitkeep
rename to docker-customization/custom-ca-certificates/.gitkeep
diff --git a/docker-customization/pip.conf b/docker-customization/pip.conf
new file mode 100644
index 00000000..3dc81272
--- /dev/null
+++ b/docker-customization/pip.conf
@@ -0,0 +1 @@
+# Add pip configuration here
\ No newline at end of file
diff --git a/docs/explanation/release_notes.md b/docs/explanation/release_notes.md
index c474eb28..0736e4bd 100644
--- a/docs/explanation/release_notes.md
+++ b/docs/explanation/release_notes.md
@@ -90,6 +90,11 @@
     *   **Files Modified**: `chat-citations.js`.
     *   (Ref: Citation parsing, page range handling, `CITATION_IMPROVEMENTS.md`)
 
+*   **Docker Customization: CA Certificate and pip.conf**
+    *   Fixed Docker customization issues related to custom CA certificate handling and `pip.conf` configuration.
+    *   Ensures Python package installation works reliably in environments requiring custom certificate trust and pip configuration.
+    *   (Ref: Docker customization, CA cert setup, `pip.conf` handling)
+
 #### User Interface Enhancements
 
 *   **Extended Document Dropdown Width**
diff --git a/docs/how-to/docker_customization.md b/docs/how-to/docker_customization.md
new file mode 100644
index 00000000..a1d50828
--- /dev/null
+++ b/docs/how-to/docker_customization.md
@@ -0,0 +1,9 @@
+# Docker Customization
+
+## Custom Certificate Authorities
+
+Add custom certificate authorities to [/docker-customization/custom-ca-certificates](/docker-customization/custom-ca-certificates/) and they will be pull in to the system CAs during docker build.  Must be in .crt format.
+
+## Custom pip.conf
+
+Add customization as needed to [/docker-customization/pip.conf](/docker-customization/pip.conf).  This will be used during docker build.
\ No newline at end of file
diff --git a/pip.conf.d/.gitkeep b/pip.conf.d/.gitkeep
deleted file mode 100644
index e69de29b..00000000