diff --git a/.github/workflows/pipeline.yaml b/.github/workflows/pipeline.yaml
index 8245a257..98d92f6b 100644
--- a/.github/workflows/pipeline.yaml
+++ b/.github/workflows/pipeline.yaml
@@ -436,7 +436,10 @@ jobs:
             ROOTLESSKIT_VERSION=${{ env.ROOTLESSKIT_VERSION }}
             TINI_VERSION=${{ env.TINI_VERSION }}
             YQ_VERSION=${{ env.YQ_VERSION }}
-          cache-from: type=gha,scope=buildkit-${{ matrix.os }}-${{ github.ref_name }}
+          cache-from: |
+            type=gha,scope=buildkit-${{ matrix.os }}-${{ github.ref_name }}
+            type=gha,scope=buildkit-${{ matrix.os }}-develop
+            type=gha,scope=buildkit-${{ matrix.os }}-main
           cache-to: type=gha,scope=buildkit-${{ matrix.os }}-${{ github.ref_name }}
           context: src/docker
           file: src/docker/Dockerfile-${{ matrix.os }}
diff --git a/src/docker/Dockerfile-bookworm b/src/docker/Dockerfile-bookworm
index 6df45697..059e9fcf 100644
--- a/src/docker/Dockerfile-bookworm
+++ b/src/docker/Dockerfile-bookworm
@@ -156,8 +156,11 @@ RUN --mount=target=/${USER}/.cache/pip,type=cache,id=pip-${PYTHON_VERSION_MAJOR_
     python3 -m pip \
         --disable-pip-version-check \
         --quiet \
+        --retries 8 \
+        --timeout 120 \
         install \
-            setuptools wheel \
+            --upgrade \
+            pip setuptools wheel \
     && find / -depth -type d -name __pycache__ -exec rm -rf {} \; 2> /dev/null
 
 # Install Azure CLI, then verify installation
@@ -167,6 +170,8 @@ RUN --mount=target=/${USER}/.cache/pip,type=cache,id=pip-${PYTHON_VERSION_MAJOR_
     python3 -m pip \
         --disable-pip-version-check \
         --quiet \
+        --retries 8 \
+        --timeout 120 \
         install \
             azure-cli==${AZURE_CLI_VERSION} \
     && az version \
diff --git a/src/docker/Dockerfile-bullseye b/src/docker/Dockerfile-bullseye
index 6582cd34..3ff13cc3 100644
--- a/src/docker/Dockerfile-bullseye
+++ b/src/docker/Dockerfile-bullseye
@@ -154,8 +154,11 @@ RUN --mount=target=/${USER}/.cache/pip,type=cache,id=pip-${PYTHON_VERSION_MAJOR_
     python3 -m pip \
         --disable-pip-version-check \
         --quiet \
+        --retries 8 \
+        --timeout 120 \
         install \
-            setuptools wheel \
+            --upgrade \
+            pip setuptools wheel \
     && find / -depth -type d -name __pycache__ -exec rm -rf {} \; 2> /dev/null
 
 # Install Azure CLI, then verify installation
@@ -165,6 +168,8 @@ RUN --mount=target=/${USER}/.cache/pip,type=cache,id=pip-${PYTHON_VERSION_MAJOR_
     python3 -m pip \
         --disable-pip-version-check \
         --quiet \
+        --retries 8 \
+        --timeout 120 \
         install \
             azure-cli==${AZURE_CLI_VERSION} \
     && az version \
diff --git a/src/docker/Dockerfile-focal b/src/docker/Dockerfile-focal
index 9d7ab409..a310d4eb 100644
--- a/src/docker/Dockerfile-focal
+++ b/src/docker/Dockerfile-focal
@@ -153,8 +153,11 @@ RUN --mount=target=/${USER}/.cache/pip,type=cache,id=pip-${PYTHON_VERSION_MAJOR_
     python3 -m pip \
         --disable-pip-version-check \
         --quiet \
+        --retries 8 \
+        --timeout 120 \
         install \
-            setuptools wheel \
+            --upgrade \
+            pip setuptools wheel \
     && find / -depth -type d -name __pycache__ -exec rm -rf {} \; 2> /dev/null
 
 # Install Azure CLI, then verify installation
@@ -164,6 +167,8 @@ RUN --mount=target=/${USER}/.cache/pip,type=cache,id=pip-${PYTHON_VERSION_MAJOR_
     python3 -m pip \
         --disable-pip-version-check \
         --quiet \
+        --retries 8 \
+        --timeout 120 \
         install \
             azure-cli==${AZURE_CLI_VERSION} \
     && az version \
diff --git a/src/docker/Dockerfile-jammy b/src/docker/Dockerfile-jammy
index 55ef39ff..25cb6f23 100644
--- a/src/docker/Dockerfile-jammy
+++ b/src/docker/Dockerfile-jammy
@@ -153,8 +153,11 @@ RUN --mount=target=/${USER}/.cache/pip,type=cache,id=pip-${PYTHON_VERSION_MAJOR_
     python3 -m pip \
         --disable-pip-version-check \
         --quiet \
+        --retries 8 \
+        --timeout 120 \
         install \
-            setuptools wheel \
+            --upgrade \
+            pip setuptools wheel \
     && find / -depth -type d -name __pycache__ -exec rm -rf {} \; 2> /dev/null
 
 # Install Azure CLI, then verify installation
@@ -164,6 +167,8 @@ RUN --mount=target=/${USER}/.cache/pip,type=cache,id=pip-${PYTHON_VERSION_MAJOR_
     python3 -m pip \
         --disable-pip-version-check \
         --quiet \
+        --retries 8 \
+        --timeout 120 \
         install \
             azure-cli==${AZURE_CLI_VERSION} \
     && az version \
diff --git a/src/docker/Dockerfile-noble b/src/docker/Dockerfile-noble
index b46f8b86..62d43a7c 100644
--- a/src/docker/Dockerfile-noble
+++ b/src/docker/Dockerfile-noble
@@ -154,8 +154,11 @@ RUN --mount=target=/${USER}/.cache/pip,type=cache,id=pip-${PYTHON_VERSION_MAJOR_
     python3 -m pip \
         --disable-pip-version-check \
         --quiet \
+        --retries 8 \
+        --timeout 120 \
         install \
-            setuptools wheel \
+            --upgrade \
+            pip setuptools wheel \
     && find / -depth -type d -name __pycache__ -exec rm -rf {} \; 2> /dev/null
 
 # Install Azure CLI, then verify installation
@@ -165,6 +168,8 @@ RUN --mount=target=/${USER}/.cache/pip,type=cache,id=pip-${PYTHON_VERSION_MAJOR_
     python3 -m pip \
         --disable-pip-version-check \
         --quiet \
+        --retries 8 \
+        --timeout 120 \
         install \
             azure-cli==${AZURE_CLI_VERSION} \
     && az version \
diff --git a/src/docker/Dockerfile-ubi8 b/src/docker/Dockerfile-ubi8
index 9d28ccfd..984bfcad 100644
--- a/src/docker/Dockerfile-ubi8
+++ b/src/docker/Dockerfile-ubi8
@@ -150,8 +150,11 @@ RUN --mount=target=/${USER}/.cache/pip,type=cache,id=pip-${PYTHON_VERSION_MAJOR_
     python3 -m pip \
         --disable-pip-version-check \
         --quiet \
+        --retries 8 \
+        --timeout 120 \
         install \
-            setuptools wheel \
+            --upgrade \
+            pip setuptools wheel \
     && find / -depth -type d -name __pycache__ -exec rm -rf {} \; 2> /dev/null
 
 # Install Azure CLI, then verify installation
@@ -161,6 +164,8 @@ RUN --mount=target=/${USER}/.cache/pip,type=cache,id=pip-${PYTHON_VERSION_MAJOR_
     python3 -m pip \
         --disable-pip-version-check \
         --quiet \
+        --retries 8 \
+        --timeout 120 \
         install \
             azure-cli==${AZURE_CLI_VERSION} \
     && az version \
diff --git a/src/docker/Dockerfile-ubi9 b/src/docker/Dockerfile-ubi9
index c407608d..e752c5db 100644
--- a/src/docker/Dockerfile-ubi9
+++ b/src/docker/Dockerfile-ubi9
@@ -149,8 +149,11 @@ RUN --mount=target=/${USER}/.cache/pip,type=cache,id=pip-${PYTHON_VERSION_MAJOR_
     python3 -m pip \
         --disable-pip-version-check \
         --quiet \
+        --retries 8 \
+        --timeout 120 \
         install \
-            setuptools wheel \
+            --upgrade \
+            pip setuptools wheel \
     && find / -depth -type d -name __pycache__ -exec rm -rf {} \; 2> /dev/null
 
 # Install Azure CLI, then verify installation
@@ -160,6 +163,8 @@ RUN --mount=target=/${USER}/.cache/pip,type=cache,id=pip-${PYTHON_VERSION_MAJOR_
     python3 -m pip \
         --disable-pip-version-check \
         --quiet \
+        --retries 8 \
+        --timeout 120 \
         install \
             azure-cli==${AZURE_CLI_VERSION} \
     && az version \
diff --git a/src/docker/Dockerfile-win-ltsc2019 b/src/docker/Dockerfile-win-ltsc2019
index 0f87878c..c46e08c3 100644
--- a/src/docker/Dockerfile-win-ltsc2019
+++ b/src/docker/Dockerfile-win-ltsc2019
@@ -53,8 +53,11 @@ RUN python --version \
         --disable-pip-version-check \
         --no-cache-dir \
         --quiet \
+        --retries 8 \
+        --timeout 120 \
         install \
-            setuptools wheel
+            --upgrade \
+            pip setuptools wheel
 
 # Install Azure CLI, then verify installation
 # TODO: Clean up "__pycache__" folders on disk
@@ -64,6 +67,8 @@ RUN python -m pip \
         --disable-pip-version-check \
         --no-cache-dir \
         --quiet \
+        --retries 8 \
+        --timeout 120 \
         install \
             "azure-cli==${Env:AZURE_CLI_VERSION}" \
     && az version
diff --git a/src/docker/Dockerfile-win-ltsc2022 b/src/docker/Dockerfile-win-ltsc2022
index ebc86c80..7e67bd51 100644
--- a/src/docker/Dockerfile-win-ltsc2022
+++ b/src/docker/Dockerfile-win-ltsc2022
@@ -53,8 +53,11 @@ RUN python --version \
         --disable-pip-version-check \
         --no-cache-dir \
         --quiet \
+        --retries 8 \
+        --timeout 120 \
         install \
-            setuptools wheel
+            --upgrade \
+            pip setuptools wheel
 
 # Install Azure CLI, then verify installation
 # TODO: Clean up "__pycache__" folders on disk
@@ -64,6 +67,8 @@ RUN python -m pip \
         --disable-pip-version-check \
         --no-cache-dir \
         --quiet \
+        --retries 8 \
+        --timeout 120 \
         install \
             "azure-cli==${Env:AZURE_CLI_VERSION}" \
     && az version