diff --git a/.devcontainer/devcontainer.json b/.devcontainer/devcontainer.json
index df755d3e1680e2..7fdbed406e3527 100644
--- a/.devcontainer/devcontainer.json
+++ b/.devcontainer/devcontainer.json
@@ -12,6 +12,7 @@
   "mounts": [
     "source=/usr/local/gitpod/config/,target=/usr/local/gitpod/config/,type=bind"
   ],
+  "onCreateCommand": "bash /workspace/gitpod/dev/setup-github-auth.sh",
   "remoteEnv": {
     "GIT_EDITOR": "code --wait",
     "KUBE_EDITOR": "code --wait"
diff --git a/.gitpod.yml b/.gitpod.yml
index 2ddaf4e6090a08..1e5a6c2ff29112 100644
--- a/.gitpod.yml
+++ b/.gitpod.yml
@@ -47,6 +47,10 @@ tasks:
       leeway run components/local-app:install-cli
       leeway run components/local-app:cli-completion
       exit 0
+  - name: Setup GitHub CLI Auth
+    init: |
+      bash /workspace/gitpod/dev/setup-github-auth.sh
+      exit 0
   # This task takes care of configuring your workspace so it can manage and interact
   # with preview environments.
   - name: Preview environment configuration
diff --git a/dev/github-token.sh b/dev/github-token.sh
new file mode 100755
index 00000000000000..8be07b2260e6e7
--- /dev/null
+++ b/dev/github-token.sh
@@ -0,0 +1,18 @@
+#!/bin/bash
+
+# GitHub Token Helper
+# Dynamically retrieves GitHub token from git credentials
+# Safe to source - will not error if git credentials are unavailable
+
+# Only set GH_TOKEN if not already set and git credential is available
+if [ -z "$GH_TOKEN" ] && command -v git >/dev/null 2>&1; then
+    # Attempt to get token from git credentials, suppress errors
+    TOKEN=$(printf 'protocol=https\nhost=github.com\n' | git credential fill 2>/dev/null | awk -F= '/password/ {print $2}' 2>/dev/null)
+    
+    # Only export if we got a non-empty token
+    if [ -n "$TOKEN" ]; then
+        export GH_TOKEN="$TOKEN"
+    fi
+    
+    unset TOKEN
+fi
diff --git a/dev/setup-github-auth.sh b/dev/setup-github-auth.sh
new file mode 100755
index 00000000000000..e04591f950da56
--- /dev/null
+++ b/dev/setup-github-auth.sh
@@ -0,0 +1,23 @@
+#!/bin/bash
+
+# GitHub CLI Authentication Setup
+# Adds sourcing of GitHub token helper to shell profiles
+
+SCRIPT_DIR="$(cd "$(dirname "${BASH_SOURCE[0]}")" && pwd)"
+GITHUB_TOKEN_HELPER="$SCRIPT_DIR/github-token.sh"
+
+{
+    echo ""
+    echo "# GitHub token helper"
+    echo "source \"$GITHUB_TOKEN_HELPER\""
+} >> ~/.bashrc
+
+{
+    echo ""
+    echo "# GitHub token helper"
+    echo "source \"$GITHUB_TOKEN_HELPER\""
+} >> ~/.zshrc
+
+source "$GITHUB_TOKEN_HELPER"
+
+echo "✅ GitHub CLI configured"