diff --git a/.github/workflows/tests.yml b/.github/workflows/tests.yml
index b14d080ba2..68ca8534ce 100644
--- a/.github/workflows/tests.yml
+++ b/.github/workflows/tests.yml
@@ -48,6 +48,7 @@ jobs:
 
       - name: Install dependencies
         run: |
+          pip3 install --upgrade pip
           pip3 install packaging
           pip3 install -U -e .
           pip3 install -r requirements-tests.txt
diff --git a/docker/Dockerfile b/docker/Dockerfile
index f8b97771d6..f59033c7b1 100644
--- a/docker/Dockerfile
+++ b/docker/Dockerfile
@@ -18,7 +18,8 @@ RUN git clone --depth=1 https://github.com/OpenAccess-AI-Collective/axolotl.git
 
 WORKDIR /workspace/axolotl
 
-RUN pip install packaging
+RUN pip install --upgrade pip && \
+    pip install packaging
 
 # If AXOLOTL_EXTRAS is set, append it in brackets
 RUN if [ "$AXOLOTL_EXTRAS" != "" ] ; then \
diff --git a/docker/Dockerfile-tests b/docker/Dockerfile-tests
index 2ec94f8684..585f68ba39 100644
--- a/docker/Dockerfile-tests
+++ b/docker/Dockerfile-tests
@@ -22,6 +22,9 @@ WORKDIR /workspace/axolotl
 RUN git fetch origin +$GITHUB_REF && \
     git checkout FETCH_HEAD
 
+RUN pip install --upgrade pip && \
+    pip install packaging \
+
 # If AXOLOTL_EXTRAS is set, append it in brackets
 RUN if [ "$AXOLOTL_EXTRAS" != "" ] ; then \
         pip install -e .[deepspeed,flash-attn,mamba-ssm,$AXOLOTL_EXTRAS]; \