diff --git a/.devcontainer/devcontainer.json b/.devcontainer/devcontainer.json
index a9339f7e0cf7e..8d16afcda362a 100644
--- a/.devcontainer/devcontainer.json
+++ b/.devcontainer/devcontainer.json
@@ -1,7 +1,6 @@
 {
 	"name": "Development environments on your infrastructure",
 	"image": "codercom/oss-dogfood:latest",
-
 	"features": {
 		// See all possible options here https://github.com/devcontainers/features/tree/main/src/docker-in-docker
 		"ghcr.io/devcontainers/features/docker-in-docker:2": {
@@ -13,10 +12,20 @@
 		}
 	},
 	// SYS_PTRACE to enable go debugging
-	"runArgs": ["--cap-add=SYS_PTRACE"],
+	"runArgs": [
+		"--cap-add=SYS_PTRACE"
+	],
 	"customizations": {
 		"vscode": {
-			"extensions": ["biomejs.biome"]
+			"extensions": [
+				"biomejs.biome"
+			]
 		}
-	}
+	},
+	"mounts": [
+		// Mount the entire home because conditional mounts are not supported.
+		// See: https://github.com/devcontainers/spec/issues/132
+		"source=${localEnv:HOME},target=/mnt/home/coder,type=bind,readonly"
+	],
+	"postCreateCommand": "./.devcontainer/postCreateCommand.sh"
 }
diff --git a/.devcontainer/postCreateCommand.sh b/.devcontainer/postCreateCommand.sh
new file mode 100755
index 0000000000000..bad584e85bea9
--- /dev/null
+++ b/.devcontainer/postCreateCommand.sh
@@ -0,0 +1,54 @@
+#!/bin/sh
+
+install_ssh_config() {
+	echo "🔑 Installing SSH configuration..."
+	rsync -a /mnt/home/coder/.ssh/ ~/.ssh/
+	chmod 0700 ~/.ssh
+}
+
+install_git_config() {
+	echo "📂 Installing Git configuration..."
+	if [ -f /mnt/home/coder/git/config ]; then
+		rsync -a /mnt/home/coder/git/ ~/.config/git/
+	elif [ -d /mnt/home/coder/.gitconfig ]; then
+		rsync -a /mnt/home/coder/.gitconfig ~/.gitconfig
+	else
+		echo "⚠️ Git configuration directory not found."
+	fi
+}
+
+install_dotfiles() {
+	if [ ! -d /mnt/home/coder/.config/coderv2/dotfiles ]; then
+		echo "⚠️ Dotfiles directory not found."
+		return
+	fi
+
+	cd /mnt/home/coder/.config/coderv2/dotfiles || return
+	for script in install.sh install bootstrap.sh bootstrap script/bootstrap setup.sh setup script/setup; do
+		if [ -x $script ]; then
+			echo "📦 Installing dotfiles..."
+			./$script || {
+				echo "❌ Error running $script. Please check the script for issues."
+				return
+			}
+			echo "✅ Dotfiles installed successfully."
+			return
+		fi
+	done
+	echo "⚠️ No install script found in dotfiles directory."
+}
+
+personalize() {
+	# Allow script to continue as Coder dogfood utilizes a hack to
+	# synchronize startup script execution.
+	touch /tmp/.coder-startup-script.done
+
+	if [ -x /mnt/home/coder/personalize ]; then
+		echo "🎨 Personalizing environment..."
+		/mnt/home/coder/personalize
+	fi
+}
+
+install_ssh_config
+install_dotfiles
+personalize