diff --git a/dogfood/coder/Dockerfile b/dogfood/coder/Dockerfile
index 1318b04df0..d74a88cdde 100644
--- a/dogfood/coder/Dockerfile
+++ b/dogfood/coder/Dockerfile
@@ -214,7 +214,11 @@ RUN sed -i 's|http://archive.ubuntu.com/ubuntu/|http://mirrors.edge.kernel.org/u
 # Install Google Chrome directly from Google. Ubuntu 22.04 ships
 # chromium-browser as a snap-only package, which does not work in
 # Docker containers.
-RUN wget -q https://dl.google.com/linux/direct/google-chrome-stable_current_amd64.deb && \
+# configure-chrome-flags.sh is automatically run after dpkg operations
+# by dogfood/coder/files/etc/apt/apt.conf.d/99-chrome-flags.
+COPY configure-chrome-flags.sh /usr/local/bin/configure-chrome-flags.sh
+RUN chmod a+x /usr/local/bin/configure-chrome-flags.sh && \
+	wget -q https://dl.google.com/linux/direct/google-chrome-stable_current_amd64.deb && \
 	apt-get install --yes ./google-chrome-stable_current_amd64.deb && \
 	rm google-chrome-stable_current_amd64.deb
 
diff --git a/dogfood/coder/configure-chrome-flags.sh b/dogfood/coder/configure-chrome-flags.sh
new file mode 100644
index 0000000000..ee2e9bbaef
--- /dev/null
+++ b/dogfood/coder/configure-chrome-flags.sh
@@ -0,0 +1,31 @@
+#!/bin/bash
+# Adds launch flags to all Google Chrome .desktop files so that Chrome
+# works correctly in headless / GPU-less environments (e.g. Coder
+# workspaces running inside Docker containers).
+#
+# This script is idempotent.
+
+set -euo pipefail
+
+CHROME_FLAGS=(
+	--use-gl=angle
+	--use-angle=swiftshader
+	--disable-dev-shm-usage
+	--no-first-run
+	--no-default-browser-check
+	--disable-background-networking
+	--disable-sync
+	--start-maximized
+)
+
+FLAGS_STR="${CHROME_FLAGS[*]}"
+
+for desktop_file in /usr/share/applications/google-chrome*.desktop /usr/share/applications/com.google.Chrome*.desktop; do
+	[ -f "$desktop_file" ] || continue
+	# Skip if flags are already present.
+	if grep -q -- '--use-gl=angle' "$desktop_file"; then
+		continue
+	fi
+	# Insert flags after the binary path on every Exec= line.
+	sed -i "s|Exec=/usr/bin/google-chrome-stable|Exec=/usr/bin/google-chrome-stable ${FLAGS_STR}|" "$desktop_file"
+done
diff --git a/dogfood/coder/files/etc/apt/apt.conf.d/99-chrome-flags b/dogfood/coder/files/etc/apt/apt.conf.d/99-chrome-flags
new file mode 100644
index 0000000000..fb74c05a04
--- /dev/null
+++ b/dogfood/coder/files/etc/apt/apt.conf.d/99-chrome-flags
@@ -0,0 +1,3 @@
+// Re-apply Chrome desktop-file flags after any package operation so
+// that a google-chrome-stable upgrade does not silently drop them.
+DPkg::Post-Invoke { "/usr/local/bin/configure-chrome-flags.sh 2>/dev/null || true"; };