diff --git a/Dockerfile b/Dockerfile
index d5d2d7e..a038ba3 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -93,8 +93,8 @@ ENV PORT=3000
 ENV PATH /app/.heroku/php/bin:/app/.heroku/php/sbin:/app/.heroku/node/bin/:/app/user/node_modules/.bin:/app/user/vendor/bin:/app/user:/opt/mssql-tools18/bin:$PATH
 
 # Install Microsoft ODBC driver, MSSQL tools and unixODBC development headers
-RUN curl https://packages.microsoft.com/keys/microsoft.asc | apt-key add - \
-    && curl https://packages.microsoft.com/config/ubuntu/24.04/prod.list > /etc/apt/sources.list.d/mssql-release.list \
+RUN curl https://packages.microsoft.com/keys/microsoft.asc | gpg --dearmor -o /usr/share/keyrings/microsoft-prod.gpg \
+    && curl https://packages.microsoft.com/config/ubuntu/24.04/prod.list | tee /etc/apt/sources.list.d/mssql-release.list \
     && apt-get update -qqy \
     && ACCEPT_EULA=Y apt-get -qqy install msodbcsql18 mssql-tools18 unixodbc-dev