diff --git a/Docker/PlexAniSync/Dockerfile b/Docker/PlexAniSync/Dockerfile
index 922785ac..aae3d52e 100644
--- a/Docker/PlexAniSync/Dockerfile
+++ b/Docker/PlexAniSync/Dockerfile
@@ -5,6 +5,7 @@ RUN apt-get update && \
     build-essential \
     && apt-get clean && rm -rf /var/lib/apt/lists/*
 
+RUN pip install --upgrade pip
 COPY requirements.txt .
 # install dependencies to the local user directory (eg. /root/.local)
 RUN pip install --user --no-warn-script-location -r requirements.txt
diff --git a/Docker/Tautulli/Dockerfile b/Docker/Tautulli/Dockerfile
index cc8fca4b..df1b2256 100644
--- a/Docker/Tautulli/Dockerfile
+++ b/Docker/Tautulli/Dockerfile
@@ -5,6 +5,7 @@ RUN apt-get update && \
     build-essential \
     && apt-get clean && rm -rf /var/lib/apt/lists/*
 
+RUN pip install --upgrade pip
 COPY requirements.txt .
 # install dependencies to the local user directory (eg. /root/.local)
 RUN pip install --user --no-warn-script-location -r requirements.txt