diff --git a/presidio-analyzer/Dockerfile.windows b/presidio-analyzer/Dockerfile.windows
index e2af573f6..cb2e24db6 100644
--- a/presidio-analyzer/Dockerfile.windows
+++ b/presidio-analyzer/Dockerfile.windows
@@ -9,6 +9,7 @@ ADD https://aka.ms/vs/16/release/vc_redist.x64.exe .
 RUN ./vc_redist.x64.exe /quiet /install
 
 COPY ./Pipfile* .
+RUN pip install --upgrade pip
 RUN pip install pipenv; pipenv install --deploy
 
 # install nlp models specified in conf/default.yaml
@@ -18,4 +19,4 @@ RUN pipenv run python install_nlp_models.py --conf_file $Env:NLP_CONF_FILE
 
 COPY . .
 EXPOSE ${PORT}
-CMD pipenv run python app.py --host 0.0.0.0
\ No newline at end of file
+CMD pipenv run python app.py --host 0.0.0.0
diff --git a/presidio-anonymizer/Dockerfile.windows b/presidio-anonymizer/Dockerfile.windows
index c9910c3d8..119d2dbcc 100644
--- a/presidio-anonymizer/Dockerfile.windows
+++ b/presidio-anonymizer/Dockerfile.windows
@@ -5,9 +5,10 @@ ENV PIP_NO_CACHE_DIR=1
 WORKDIR /app
 
 COPY ./Pipfile* .
+RUN pip install --upgrade pip
 RUN pip install pipenv; pipenv install --deploy
 
 COPY . .
 
 EXPOSE ${PORT}
-CMD pipenv run python app.py
\ No newline at end of file
+CMD pipenv run python app.py