diff --git a/ci/dev/update-vscode.sh b/ci/dev/update-vscode.sh
index 3ae7090a..0c05a490 100755
--- a/ci/dev/update-vscode.sh
+++ b/ci/dev/update-vscode.sh
@@ -1,6 +1,33 @@
 #!/usr/bin/env bash
+# Description: This is a script to make the process of updating vscode versions easier
+# Run it with `yarn update:vscode` and it will do the following:
+# 1. Check that you have a remote called `vscode`
+# 2. Ask you which version you want to upgrade to
+# 3. Grab the exact version from the package.json i.e. 1.53.2
+# 4. Fetch the vscode remote branches to run the subtree update
+# 5. Run the subtree update and pull in the vscode update
+# 6. Commit the changes (including merge conflicts)
+# 7. Open a draft PR
+
 set -euo pipefail
 
+# This function expects two arguments
+# 1. the vscode version we're updating to
+# 2. the list of merge conflict files
+make_pr_body() {
+  local BODY="This PR updates vscode to $1
+
+## TODOS
+
+- [ ] test editor locally
+- [ ] test terminal locally
+- [ ] make notes about any significant changes in docs/CONTRIBUTING.md#notes-about-changes
+
+## Files with conflicts (fix these)
+$2"
+  echo "$BODY"
+}
+
 main() {
   cd "$(dirname "$0")/../.."
 
@@ -8,9 +35,8 @@ main() {
   # if it doesn't, we add it
   if ! git config remote.vscode.url > /dev/null; then
     echo "Could not find 'vscode' as a remote"
-    echo "Adding with: git remote add -f vscode https://github.com/microsoft/vscode.git &> /dev/null"
-    echo "Supressing output with '&> /dev/null'"
-    git remote add -f vscode https://github.com/microsoft/vscode.git &> /dev/null
+    echo "Adding with: git remote add vscode https://github.com/microsoft/vscode.git"
+    git remote add vscode https://github.com/microsoft/vscode.git
   fi
 
   # Ask which version we should update to
@@ -25,7 +51,24 @@ main() {
     exit 1
   fi
 
-  echo -e "Great! We'll prep a PR for updating to $VSCODE_VERSION_TO_UPDATE\n"
+  # Check that they have jq installed
+  if ! command -v jq &> /dev/null; then
+    echo "jq could not be found."
+    echo "We use this when looking up the exact version to update to in the package.json in VS Code."
+    echo -e "See docs here: https://stedolan.github.io/jq/download/"
+    exit
+  fi
+
+  # Grab the exact version from package.json
+  VSCODE_EXACT_VERSION=$(curl -s "https://raw.githubusercontent.com/microsoft/vscode/release/$VSCODE_VERSION_TO_UPDATE/package.json" | jq -r ".version")
+
+  echo -e "Great! We'll prep a PR for updating to $VSCODE_EXACT_VERSION\n"
+
+  # For some reason the subtree update doesn't work
+  # unless we fetch all the branches
+  echo -e "Fetching vscode branches..."
+  echo -e "Note: this might take a while"
+  git fetch vscode
 
   # Check if GitHub CLI is installed
   if ! command -v gh &> /dev/null; then
@@ -42,17 +85,36 @@ main() {
   if [[ -z $(git ls-remote --heads origin "$CURRENT_BRANCH") ]]; then
     echo "Doesn't look like you've pushed this branch to remote"
     echo -e "Pushing now using: git push origin $CURRENT_BRANCH\n"
-    git push origin "$CURRENT_BRANCH"
+    # Note: we need to set upstream as well or the gh pr create step will fail
+    # See: https://github.com/cli/cli/issues/575
+    git push -u origin "$CURRENT_BRANCH"
   fi
 
-  echo "Opening a draft PR on GitHub"
-  # To read about these flags, visit the docs: https://cli.github.com/manual/gh_pr_create
-  gh pr create --base master --title "feat(vscode): update to version $VSCODE_VERSION_TO_UPDATE" --body "This PR updates vscode to version: $VSCODE_VERSION_TO_UPDATE" --reviewer @cdr/code-server-reviewers --repo cdr/code-server --draft
-
   echo "Going to try to update vscode for you..."
   echo -e "Running: git subtree pull --prefix lib/vscode vscode release/${VSCODE_VERSION_TO_UPDATE} --squash\n"
   # Try to run subtree update command
-  git subtree pull --prefix lib/vscode vscode release/"${VSCODE_VERSION_TO_UPDATE}" --squash --message "chore(vscode): update to $VSCODE_VERSION_TO_UPDATE"
+  # Note: we add `|| true` because we want the script to keep running even if the squash fails
+  # We know the squash fails everytime because there will always be merge conflicts
+  git subtree pull --prefix lib/vscode vscode release/"${VSCODE_VERSION_TO_UPDATE}" --squash || true
+
+  # Get the files with conflicts before we commit them
+  # so we can list them in the PR body
+  CONFLICTS=$(git diff --name-only --diff-filter=U | while read -r line; do echo "- $line"; done)
+  PR_BODY=$(make_pr_body "$VSCODE_EXACT_VERSION" "$CONFLICTS")
+
+  echo -e "\nForcing a commit with conflicts"
+  echo "Note: this is intentional"
+  echo "If we don't do this, code review is impossible."
+  echo -e "For more info, see docs: docs/CONTRIBUTING.md#updating-vs-code\n"
+  # We need --no-verify to skip the husky pre-commit hook
+  # which fails because of the merge conflicts
+  git add . && git commit -am "chore(vscode): update to $VSCODE_EXACT_VERSION" --no-verify
+
+  # Note: we can't open a draft PR unless their are changes.
+  # Hence why we do this after the subtree update.
+  echo "Opening a draft PR on GitHub"
+  # To read about these flags, visit the docs: https://cli.github.com/manual/gh_pr_create
+  gh pr create --base main --title "feat(vscode): update to version $VSCODE_EXACT_VERSION" --body "$PR_BODY" --reviewer @cdr/code-server-reviewers --repo cdr/code-server --draft
 }
 
 main "$@"