diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 2ec0d9f3..ca7a43a8 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -75,3 +75,5 @@ jobs:
         uses: ./.github/actions/nix-devshell
 
       - run: make lint
+        env:
+          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
diff --git a/.github/workflows/release.yml b/.github/workflows/release.yml
index 4c2e8780..70c4cdc0 100644
--- a/.github/workflows/release.yml
+++ b/.github/workflows/release.yml
@@ -1,6 +1,9 @@
 name: release
 
 on:
+  push:
+    branches:
+      - main
   release:
     types: [published]
 
@@ -8,6 +11,7 @@ permissions: {}
 
 jobs:
   build:
+    name: Build Coder Desktop
     runs-on: ${{ github.repository_owner == 'coder' && 'depot-macos-latest' || 'macos-latest'}}
     if: ${{ github.repository_owner == 'coder' }}
     permissions:
@@ -40,7 +44,34 @@ jobs:
         run: make release
 
       - name: Upload Release Assets
-        run: gh release upload "$RELEASE_TAG" "$out"/*
+        run: gh release upload "$RELEASE_TAG" "$out"/* --clobber
         env:
-          GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
-          RELEASE_TAG: ${{ github.event.release.tag_name }}
+          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+          RELEASE_TAG: ${{ github.event_name == 'release' && github.event.release.tag_name || 'preview' }}
+
+  update-cask:
+    name: Update homebrew-coder cask
+    runs-on: ${{ github.repository_owner == 'coder' && 'depot-macos-latest' || 'macos-latest'}}
+    if: ${{ github.repository_owner == 'coder' }}
+    needs: build
+    steps:
+      - name: Checkout
+        uses: actions/checkout@11bd71901bbe5b1630ceea73d27597364c9af683 # v4.2.2
+        with:
+          fetch-depth: 1
+          persist-credentials: false
+
+      - name: Setup Nix
+        uses: ./.github/actions/nix-devshell
+
+      - name: Update homebrew-coder
+        env:
+          GH_TOKEN: ${{ secrets.CODERCI_GITHUB_TOKEN }}
+          RELEASE_TAG: ${{ github.event_name == 'release' && github.event.release.tag_name || 'preview' }}
+          ASSIGNEE: ${{ github.actor }}
+        run: |
+          git config --global user.email "ci@coder.com"
+          git config --global user.name "Coder CI"
+          gh auth setup-git
+
+          ./scripts/update-cask.sh --version "$RELEASE_TAG" --assignee "$ASSIGNEE"
diff --git a/Makefile b/Makefile
index 81fe6723..ee073008 100644
--- a/Makefile
+++ b/Makefile
@@ -11,12 +11,12 @@ XCPROJECT := Coder\ Desktop/Coder\ Desktop.xcodeproj
 SCHEME := Coder\ Desktop
 SWIFT_VERSION := 6.0
 
-CURRENT_PROJECT_VERSION=$(shell git describe --tags)
+CURRENT_PROJECT_VERSION:=$(shell git describe --match 'v[0-9]*' --dirty='.devel' --always --tags)
 ifeq ($(strip $(CURRENT_PROJECT_VERSION)),)
     $(error CURRENT_PROJECT_VERSION cannot be empty)
 endif
 
-MARKETING_VERSION=$(shell git describe --tags --abbrev=0 | sed 's/^v//' | sed 's/-.*$$//')
+MARKETING_VERSION:=$(shell git describe --match 'v[0-9]*' --tags --abbrev=0 | sed 's/^v//' | sed 's/-.*$$//')
 ifeq ($(strip $(MARKETING_VERSION)),)
     $(error MARKETING_VERSION cannot be empty)
 endif
@@ -132,3 +132,5 @@ help: ## Show this help
 .PHONY: watch-gen
 watch-gen: ## Generate Xcode project file and watch for changes
 	watchexec -w 'Coder Desktop/project.yml' make $(XCPROJECT)
+
+print-%: ; @echo $*=$($*)
diff --git a/scripts/update-cask.sh b/scripts/update-cask.sh
new file mode 100755
index 00000000..01f25827
--- /dev/null
+++ b/scripts/update-cask.sh
@@ -0,0 +1,123 @@
+#!/usr/bin/env bash
+set -euo pipefail
+
+usage() {
+  echo "Usage: $0 [--version <version>] [--assignee <github handle>]"
+  echo "  --version  <version>        Set the VERSION variable to fetch and generate the cask file for"
+  echo "  --assignee <github handle>  Set the ASSIGNE variable to assign the PR to (optional)"
+  echo "  -h, --help                  Display this help message"
+}
+
+VERSION=""
+ASSIGNE=""
+
+# Parse command line arguments
+while [[ "$#" -gt 0 ]]; do
+  case $1 in
+  --version)
+    VERSION="$2"
+    shift 2
+    ;;
+  --assignee)
+    ASSIGNE="$2"
+    shift 2
+    ;;
+  -h | --help)
+    usage
+    exit 0
+    ;;
+  *)
+    echo "Unknown parameter passed: $1"
+    usage
+    exit 1
+    ;;
+  esac
+done
+
+# Assert version is not empty and starts with v
+[ -z "$VERSION" ] && {
+  echo "Error: VERSION cannot be empty"
+  exit 1
+}
+[[ "$VERSION" =~ ^v || "$VERSION" == "preview" ]] || {
+  echo "Error: VERSION must start with a 'v'"
+  exit 1
+}
+
+# Download the Coder Desktop dmg
+GH_RELEASE_FOLDER=$(mktemp -d)
+
+gh release download "$VERSION" \
+  --repo coder/coder-desktop-macos \
+  --dir "$GH_RELEASE_FOLDER" \
+  --pattern 'Coder.Desktop.dmg'
+
+HASH=$(shasum -a 256 "$GH_RELEASE_FOLDER"/Coder.Desktop.dmg | awk '{print $1}' | tr -d '\n')
+
+IS_PREVIEW=false
+if [[ "$VERSION" == "preview" ]]; then
+  IS_PREVIEW=true
+  VERSION=$(make 'print-CURRENT_PROJECT_VERSION' | sed 's/CURRENT_PROJECT_VERSION=//g')
+fi
+
+# Check out the homebrew tap repo
+TAP_CHECHOUT_FOLDER=$(mktemp -d)
+
+gh repo clone "coder/homebrew-coder" "$TAP_CHECHOUT_FOLDER"
+
+cd "$TAP_CHECHOUT_FOLDER"
+
+BREW_BRANCH="auto-release/desktop-$VERSION"
+
+# Check if a PR already exists.
+# Continue on a main branch release, as the sha256 will change.
+pr_count="$(gh pr list --search "head:$BREW_BRANCH" --json id,closed | jq -r ".[] | select(.closed == false) | .id" | wc -l)"
+if [[ "$pr_count" -gt 0 && "$IS_PREVIEW" == false ]]; then
+  echo "Bailing out as PR already exists" 2>&1
+  exit 0
+fi
+
+git checkout -b "$BREW_BRANCH"
+
+# If this is a main branch build, append a preview suffix to the cask.
+SUFFIX=""
+CONFLICTS_WITH="coder-desktop-preview"
+TAG=$VERSION
+if [[ "$IS_PREVIEW" == true ]]; then
+  SUFFIX="-preview"
+  CONFLICTS_WITH="coder-desktop"
+  TAG="preview"
+fi
+
+mkdir -p "$TAP_CHECHOUT_FOLDER"/Casks
+
+# Overwrite the cask file
+cat >"$TAP_CHECHOUT_FOLDER"/Casks/coder-desktop${SUFFIX}.rb <<EOF
+cask "coder-desktop${SUFFIX}" do
+  version "${VERSION#v}"
+  sha256 "${HASH}"
+
+  url "https://github.com/coder/coder-desktop-macos/releases/download/${TAG}/Coder.Desktop.dmg"
+  name "Coder Desktop"
+  desc "Coder Desktop client"
+  homepage "https://github.com/coder/coder-desktop-macos"
+
+  depends_on macos: ">= :sonoma"
+
+  app "Coder Desktop.app"
+  conflicts_with cask: "coder/coder/${CONFLICTS_WITH}"
+end
+EOF
+
+git add .
+git commit -m "Coder Desktop $VERSION"
+git push -u origin -f "$BREW_BRANCH"
+
+# Create a PR only if none exists
+if [[ "$pr_count" -eq 0 ]]; then
+  gh pr create \
+    --base master --head "$BREW_BRANCH" \
+    --title "Coder Desktop $VERSION" \
+    --body "This automatic PR was triggered by the release of Coder Desktop $VERSION" \
+    ${ASSIGNE:+ --assignee "$ASSIGNE" --reviewer "$ASSIGNE"}
+fi

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