diff --git a/Dockerfile b/Dockerfile
index c0cc0d8..b98b43d 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -16,13 +16,14 @@ RUN         apt update -y \
 # Install Wine and dependencies
 RUN         dpkg --add-architecture i386 \
             && apt update -y \
-            && apt install -y software-properties-common gnupg2 \
-            && wget -qO - https://dl.winehq.org/wine-builds/winehq.key | apt-key add - \
-            && echo "deb https://dl.winehq.org/wine-builds/debian/ bullseye main" >> /etc/apt/sources.list.d/winehq.list \
+            && apt install -y software-properties-common gnupg2 ca-certificates \
+            && wget -qO - https://dl.winehq.org/wine-builds/winehq.key | gpg --dearmor -o /usr/share/keyrings/winehq-archive-keyring.gpg \
+            && echo "deb [signed-by=/usr/share/keyrings/winehq-archive-keyring.gpg] https://dl.winehq.org/wine-builds/debian/ bullseye main" >> /etc/apt/sources.list.d/winehq.list \
             && apt update -y \
             && apt install -y winehq-stable \
-            && apt install -y winetricks \
-            && apt install -y xvfb \
+            && apt install -y xvfb cabextract \
+            && wget -q https://raw.githubusercontent.com/Winetricks/winetricks/master/src/winetricks -O /usr/local/bin/winetricks \
+            && chmod +x /usr/local/bin/winetricks \
             && apt clean \
             && rm -rf /var/lib/apt/lists/*            
 USER        container
@@ -33,19 +34,13 @@ ENV         WINEARCH=win64
 ENV         WINEPREFIX=/home/container/.wine
 ENV         DISPLAY=:99.0
 
-# Initialize Wine prefix as container user
-RUN         Xvfb :99 -screen 0 1024x768x16 & \
-            export DISPLAY=:99.0 && \
-            wine --version && \
-            wineboot --init && \
-            winetricks -q corefonts && \
-            pkill Xvfb
-
 WORKDIR     /home/container
 
 STOPSIGNAL SIGINT
 
 COPY        --chown=container:container ./../entrypoint.sh /entrypoint.sh
+COPY        --chown=container:container ./../test-wine-dotnet.sh /test-wine-dotnet.sh
 RUN         chmod +x /entrypoint.sh
+RUN         chmod +x /test-wine-dotnet.sh
 ENTRYPOINT    ["/usr/bin/tini", "-g", "--"]
 CMD         ["/entrypoint.sh"]
\ No newline at end of file
diff --git a/entrypoint.sh b/entrypoint.sh
index 4220dcb..e2fdb39 100644
--- a/entrypoint.sh
+++ b/entrypoint.sh
@@ -12,6 +12,14 @@ export DOTNET_ROOT=/usr/share/
 Xvfb :99 -screen 0 1024x768x16 &
 export DISPLAY=:99.0
 
+# Initialize Wine prefix if it doesn't exist
+if [ ! -d "$WINEPREFIX" ]; then
+    echo "Initializing Wine prefix..."
+    wineboot --init
+    winetricks -q corefonts
+    echo "Wine initialization complete."
+fi
+
 # print the dotnet version on startup
 printf "\033[1m\033[33mcontainer@pelican~ \033[0mdotnet --version\n"
 dotnet --version
diff --git a/test-wine-dotnet.sh b/test-wine-dotnet.sh
new file mode 100644
index 0000000..97fc7f1
--- /dev/null
+++ b/test-wine-dotnet.sh
@@ -0,0 +1,24 @@
+#!/bin/bash
+
+echo "Testing Wine + .NET integration..."
+
+# Test 1: Check if .NET works natively
+echo "1. Testing native .NET:"
+dotnet --version
+
+# Test 2: Check if Wine works
+echo "2. Testing Wine:"
+wine --version
+
+# Test 3: Test Wine with .NET (this will use .NET through Wine)
+echo "3. Testing .NET through Wine:"
+wine dotnet --version
+
+# Test 4: Create a simple .NET console app and run it through Wine
+echo "4. Creating and running a simple .NET app through Wine:"
+dotnet new console -n TestApp -o /tmp/testapp
+cd /tmp/testapp
+dotnet build
+wine dotnet /tmp/testapp/bin/Debug/net9.0/TestApp.dll
+
+echo "Wine + .NET integration test completed!"