diff --git a/apps/calendar/apps/web/docker-entrypoint.sh b/apps/calendar/apps/web/docker-entrypoint.sh
index 455ffc64b..df8e2168d 100644
--- a/apps/calendar/apps/web/docker-entrypoint.sh
+++ b/apps/calendar/apps/web/docker-entrypoint.sh
@@ -22,5 +22,10 @@ EOF
 echo "✅ Configuration generated at /app/apps/calendar/apps/web/build/client/config.json"
 cat /app/apps/calendar/apps/web/build/client/config.json
 
+# Remove pre-compressed versions (SvelteKit serves these instead of the raw file)
+rm -f /app/apps/calendar/apps/web/build/client/config.json.br
+rm -f /app/apps/calendar/apps/web/build/client/config.json.gz
+echo "🗑️  Removed stale pre-compressed config files"
+
 echo "🚀 Starting Calendar web app..."
 exec "$@"
diff --git a/apps/chat/apps/web/docker-entrypoint.sh b/apps/chat/apps/web/docker-entrypoint.sh
index 5a703b786..caeac21b2 100644
--- a/apps/chat/apps/web/docker-entrypoint.sh
+++ b/apps/chat/apps/web/docker-entrypoint.sh
@@ -22,5 +22,10 @@ EOF
 echo "✅ Configuration generated at /app/apps/chat/apps/web/build/client/config.json"
 cat /app/apps/chat/apps/web/build/client/config.json
 
+# Remove pre-compressed versions (SvelteKit serves these instead of the raw file)
+rm -f /app/apps/chat/apps/web/build/client/config.json.br
+rm -f /app/apps/chat/apps/web/build/client/config.json.gz
+echo "🗑️  Removed stale pre-compressed config files"
+
 echo "🚀 Starting Chat web app..."
 exec "$@"
diff --git a/apps/clock/apps/web/docker-entrypoint.sh b/apps/clock/apps/web/docker-entrypoint.sh
index dab2ca2f0..8eb1ee772 100644
--- a/apps/clock/apps/web/docker-entrypoint.sh
+++ b/apps/clock/apps/web/docker-entrypoint.sh
@@ -22,5 +22,10 @@ EOF
 echo "✅ Configuration generated at /app/apps/clock/apps/web/build/client/config.json"
 cat /app/apps/clock/apps/web/build/client/config.json
 
+# Remove pre-compressed versions (SvelteKit serves these instead of the raw file)
+rm -f /app/apps/clock/apps/web/build/client/config.json.br
+rm -f /app/apps/clock/apps/web/build/client/config.json.gz
+echo "🗑️  Removed stale pre-compressed config files"
+
 echo "🚀 Starting Clock web app..."
 exec "$@"
diff --git a/apps/contacts/apps/web/docker-entrypoint.sh b/apps/contacts/apps/web/docker-entrypoint.sh
index 12ecfe6d3..e8f9427a4 100644
--- a/apps/contacts/apps/web/docker-entrypoint.sh
+++ b/apps/contacts/apps/web/docker-entrypoint.sh
@@ -22,5 +22,10 @@ EOF
 echo "✅ Configuration generated at /app/apps/contacts/apps/web/build/client/config.json"
 cat /app/apps/contacts/apps/web/build/client/config.json
 
+# Remove pre-compressed versions (SvelteKit serves these instead of the raw file)
+rm -f /app/apps/contacts/apps/web/build/client/config.json.br
+rm -f /app/apps/contacts/apps/web/build/client/config.json.gz
+echo "🗑️  Removed stale pre-compressed config files"
+
 echo "🚀 Starting Contacts web app..."
 exec "$@"
diff --git a/apps/manacore/apps/web/docker-entrypoint.sh b/apps/manacore/apps/web/docker-entrypoint.sh
index 9ab2a028e..cfcc3c580 100755
--- a/apps/manacore/apps/web/docker-entrypoint.sh
+++ b/apps/manacore/apps/web/docker-entrypoint.sh
@@ -33,6 +33,11 @@ EOF
 echo "✅ Runtime configuration generated:"
 cat build/client/config.json
 
+# Remove pre-compressed versions (SvelteKit serves these instead of the raw file)
+rm -f build/client/config.json.br
+rm -f build/client/config.json.gz
+echo "🗑️  Removed stale pre-compressed config files"
+
 echo ""
 echo "🚀 Starting Node server..."