diff --git a/tutorials-and-examples/inference-servers/checkpoints/Dockerfile b/tutorials-and-examples/inference-servers/checkpoints/Dockerfile
index f1c6cd871..527d01577 100644
--- a/tutorials-and-examples/inference-servers/checkpoints/Dockerfile
+++ b/tutorials-and-examples/inference-servers/checkpoints/Dockerfile
@@ -13,6 +13,8 @@ RUN apt -y update && apt install -y --no-install-recommends \
     curl \
     gnupg
 
+RUN python3 -m pip install --upgrade pip
+
 RUN update-alternatives --install \
     /usr/bin/python3 python3 /usr/bin/python3.10 1
 
diff --git a/tutorials-and-examples/inference-servers/jetstream/pytorch/jetstream-pytorch-server/Dockerfile b/tutorials-and-examples/inference-servers/jetstream/pytorch/jetstream-pytorch-server/Dockerfile
index a4bc13a58..84c2d89ca 100644
--- a/tutorials-and-examples/inference-servers/jetstream/pytorch/jetstream-pytorch-server/Dockerfile
+++ b/tutorials-and-examples/inference-servers/jetstream/pytorch/jetstream-pytorch-server/Dockerfile
@@ -12,6 +12,8 @@ RUN apt -y update && apt install -y --no-install-recommends \
     python3.10 \
     python3-pip
 
+RUN python3 -m pip install --upgrade pip
+
 RUN update-alternatives --install \
     /usr/bin/python3 python3 /usr/bin/python3.10 1