diff --git a/.github/workflows/codeql.yml b/.github/workflows/codeql.yml
deleted file mode 100644
index c3d1b65ae6..0000000000
--- a/.github/workflows/codeql.yml
+++ /dev/null
@@ -1,67 +0,0 @@
-name: "CodeQL"
-
-permissions:
-  security-events: write
-
-on:
-  push:
-    branches: ["main"]
-  pull_request:
-    # The branches below must be a subset of the branches above
-    branches: ["main"]
-  schedule:
-    # run every week at 10:24 on Thursday
-    - cron: "24 10 * * 4"
-
-jobs:
-  analyze:
-    name: Analyze
-    runs-on: ubuntu-latest
-    permissions:
-      actions: read
-      contents: read
-      security-events: write
-
-    strategy:
-      fail-fast: false
-      matrix:
-        language: ["go", "javascript"]
-
-    steps:
-      - name: Checkout repository
-        uses: actions/checkout@v3
-
-      - name: Initialize CodeQL
-        uses: github/codeql-action/init@v2
-        with:
-          languages: ${{ matrix.language }}
-
-      - name: Setup Go
-        if: matrix.language == 'go'
-        uses: actions/setup-go@v3
-        with:
-          go-version: "~1.19"
-
-      - name: Go Cache Paths
-        if: matrix.language == 'go'
-        id: go-cache-paths
-        run: |
-          echo "::set-output name=go-mod::$(go env GOMODCACHE)"
-
-      - name: Go Mod Cache
-        if: matrix.language == 'go'
-        uses: actions/cache@v3
-        with:
-          path: ${{ steps.go-cache-paths.outputs.go-mod }}
-          key: ${{ runner.os }}-release-go-mod-${{ hashFiles('**/go.sum') }}
-
-      - name: Remove Makefile # workaround to prevent CodeQL from building site
-        if: matrix.language == 'go'
-        run: |
-          # Disable Analysis step from trying to build the project.
-          rm Makefile
-
-      - name: Perform CodeQL Analysis
-        uses: github/codeql-action/analyze@v2
-        with:
-          category: "/language:${{matrix.language}}"
diff --git a/.github/workflows/coder.yaml b/.github/workflows/coder.yaml
index 37ce3bd17e..055ea4f896 100644
--- a/.github/workflows/coder.yaml
+++ b/.github/workflows/coder.yaml
@@ -198,19 +198,19 @@ jobs:
       - name: Echo Go Cache Paths
         id: go-cache-paths
         run: |
-          echo "::set-output name=go-build::$(go env GOCACHE)"
-          echo "::set-output name=go-mod::$(go env GOMODCACHE)"
+          echo "GOCACHE=$(go env GOCACHE)" >> $GITHUB_OUTPUT
+          echo "GOMODCACHE=$(go env GOMODCACHE)" >> $GITHUB_OUTPUT
 
       - name: Go Build Cache
         uses: actions/cache@v3
         with:
-          path: ${{ steps.go-cache-paths.outputs.go-build }}
+          path: ${{ steps.go-cache-paths.outputs.GOCACHE }}
           key: ${{ github.job }}-go-build-${{ hashFiles('**/go.sum', '**/**.go') }}
 
       - name: Go Mod Cache
         uses: actions/cache@v3
         with:
-          path: ${{ steps.go-cache-paths.outputs.go-mod }}
+          path: ${{ steps.go-cache-paths.outputs.GOMODCACHE }}
           key: ${{ github.job }}-go-mod-${{ hashFiles('**/go.sum') }}
 
       - name: Install sqlc
@@ -296,22 +296,25 @@ jobs:
         with:
           go-version: "~1.19"
 
+      # Sadly the new "set output" syntax (of writing env vars to
+      # $GITHUB_OUTPUT) does not work on both powershell and bash so we use the
+      # deprecated syntax here.
       - name: Echo Go Cache Paths
         id: go-cache-paths
         run: |
-          echo "::set-output name=go-build::$(go env GOCACHE)"
-          echo "::set-output name=go-mod::$(go env GOMODCACHE)"
+          echo "::set-output name=GOCACHE::$(go env GOCACHE)"
+          echo "::set-output name=GOMODCACHE::$(go env GOMODCACHE)"
 
       - name: Go Build Cache
         uses: actions/cache@v3
         with:
-          path: ${{ steps.go-cache-paths.outputs.go-build }}
+          path: ${{ steps.go-cache-paths.outputs.GOCACHE }}
           key: ${{ runner.os }}-go-build-${{ hashFiles('**/go.**', '**.go') }}
 
       - name: Go Mod Cache
         uses: actions/cache@v3
         with:
-          path: ${{ steps.go-cache-paths.outputs.go-mod }}
+          path: ${{ steps.go-cache-paths.outputs.GOMODCACHE }}
           key: ${{ runner.os }}-go-mod-${{ hashFiles('**/go.sum') }}
 
       - name: Install gotestsum
@@ -335,10 +338,10 @@ jobs:
           # prevents test caching, so we disable it on alternate operating
           # systems.
           if [ "${{ matrix.os }}" == "ubuntu-latest" ]; then
-            echo ::set-output name=cover::true
+            echo "cover=true" >> $GITHUB_OUTPUT
             export COVERAGE_FLAGS='-covermode=atomic -coverprofile="gotests.coverage" -coverpkg=./...'
           else
-            echo ::set-output name=cover::false
+            echo "cover=false" >> $GITHUB_OUTPUT
           fi
 
           gotestsum --junitfile="gotests.xml" --packages="./..." -- -parallel=8 -timeout=5m -short -failfast $COVERAGE_FLAGS
@@ -380,19 +383,19 @@ jobs:
       - name: Echo Go Cache Paths
         id: go-cache-paths
         run: |
-          echo "::set-output name=go-build::$(go env GOCACHE)"
-          echo "::set-output name=go-mod::$(go env GOMODCACHE)"
+          echo "GOCACHE=$(go env GOCACHE)" >> $GITHUB_OUTPUT
+          echo "GOMODCACHE=$(go env GOMODCACHE)" >> $GITHUB_OUTPUT
 
       - name: Go Build Cache
         uses: actions/cache@v3
         with:
-          path: ${{ steps.go-cache-paths.outputs.go-build }}
+          path: ${{ steps.go-cache-paths.outputs.GOCACHE }}
           key: ${{ runner.os }}-go-build-${{ hashFiles('**/go.sum', '**/**.go') }}
 
       - name: Go Mod Cache
         uses: actions/cache@v3
         with:
-          path: ${{ steps.go-cache-paths.outputs.go-mod }}
+          path: ${{ steps.go-cache-paths.outputs.GOMODCACHE }}
           key: ${{ runner.os }}-go-mod-${{ hashFiles('**/go.sum') }}
 
       - name: Install gotestsum
@@ -429,7 +432,7 @@ jobs:
         with:
           token: ${{ secrets.CODECOV_TOKEN }}
           files: ./gotests.coverage
-          flags: unittest-go-postgres-${{ matrix.os }}
+          flags: unittest-go-postgres-linux
 
   deploy:
     name: "deploy"
@@ -463,19 +466,19 @@ jobs:
       - name: Echo Go Cache Paths
         id: go-cache-paths
         run: |
-          echo "::set-output name=go-build::$(go env GOCACHE)"
-          echo "::set-output name=go-mod::$(go env GOMODCACHE)"
+          echo "GOCACHE=$(go env GOCACHE)" >> $GITHUB_OUTPUT
+          echo "GOMODCACHE=$(go env GOMODCACHE)" >> $GITHUB_OUTPUT
 
       - name: Go Build Cache
         uses: actions/cache@v3
         with:
-          path: ${{ steps.go-cache-paths.outputs.go-build }}
+          path: ${{ steps.go-cache-paths.outputs.GOCACHE }}
           key: ${{ runner.os }}-release-go-build-${{ hashFiles('**/go.sum') }}
 
       - name: Go Mod Cache
         uses: actions/cache@v3
         with:
-          path: ${{ steps.go-cache-paths.outputs.go-mod }}
+          path: ${{ steps.go-cache-paths.outputs.GOMODCACHE }}
           key: ${{ runner.os }}-release-go-mod-${{ hashFiles('**/go.sum') }}
 
       - name: Cache Node
@@ -607,19 +610,19 @@ jobs:
       - name: Echo Go Cache Paths
         id: go-cache-paths
         run: |
-          echo "::set-output name=go-build::$(go env GOCACHE)"
-          echo "::set-output name=go-mod::$(go env GOMODCACHE)"
+          echo "GOCACHE=$(go env GOCACHE)" >> $GITHUB_OUTPUT
+          echo "GOMODCACHE=$(go env GOMODCACHE)" >> $GITHUB_OUTPUT
 
       - name: Go Build Cache
         uses: actions/cache@v3
         with:
-          path: ${{ steps.go-cache-paths.outputs.go-build }}
+          path: ${{ steps.go-cache-paths.outputs.GOCACHE }}
           key: ${{ runner.os }}-go-build-${{ hashFiles('**/go.sum') }}
 
       - name: Go Mod Cache
         uses: actions/cache@v3
         with:
-          path: ${{ steps.go-cache-paths.outputs.go-mod }}
+          path: ${{ steps.go-cache-paths.outputs.GOMODCACHE }}
           key: ${{ runner.os }}-go-mod-${{ hashFiles('**/go.sum') }}
 
       - name: Build
diff --git a/.github/workflows/dogfood.yaml b/.github/workflows/dogfood.yaml
index 0dede0bf1b..b93b6ba16f 100644
--- a/.github/workflows/dogfood.yaml
+++ b/.github/workflows/dogfood.yaml
@@ -25,7 +25,7 @@ jobs:
           tag=${{ steps.branch-name.outputs.current_branch }}
           # Replace / with --, e.g. user/feature => user--feature.
           tag=${tag//\//--}
-          echo "::set-output name=tag::${tag}"
+          echo "tag=${tag}" >> $GITHUB_OUTPUT
 
       - name: Set up QEMU
         uses: docker/setup-qemu-action@v2
@@ -54,7 +54,7 @@ jobs:
         uses: actions/checkout@v3
       - name: Get short commit SHA
         id: vars
-        run: echo "::set-output name=sha_short::$(git rev-parse --short HEAD)"
+        run: echo "sha_short=$(git rev-parse --short HEAD)" >> $GITHUB_OUTPUT
       - name: "Install latest Coder"
         run: |
           curl -L https://coder.com/install.sh | sh
diff --git a/.github/workflows/security.yaml b/.github/workflows/security.yaml
new file mode 100644
index 0000000000..3addc3d8b8
--- /dev/null
+++ b/.github/workflows/security.yaml
@@ -0,0 +1,135 @@
+name: "Security"
+
+permissions:
+  actions: read
+  contents: read
+  security-events: write
+
+on:
+  push:
+    branches: ["main"]
+
+  pull_request:
+    branches: ["main"]
+
+  workflow_dispatch:
+
+  schedule:
+    # Run every week at 10:24 on Thursday.
+    - cron: "24 10 * * 4"
+
+# Cancel in-progress runs for pull requests when developers push
+# additional changes
+concurrency:
+  group: ${{ github.workflow }}-${{ github.ref }}-security
+  cancel-in-progress: ${{ github.event_name == 'pull_request' }}
+
+jobs:
+  codeql:
+    name: CodeQL
+    runs-on: ${{ github.repository_owner == 'coder' && 'ubuntu-latest-16-cores' || 'ubuntu-latest' }}
+    strategy:
+      fail-fast: false
+      matrix:
+        language: ["go", "javascript"]
+
+    steps:
+      - name: Checkout repository
+        uses: actions/checkout@v3
+
+      - name: Initialize CodeQL
+        uses: github/codeql-action/init@v2
+        with:
+          languages: ${{ matrix.language }}
+
+      - name: Setup Go
+        if: matrix.language == 'go'
+        uses: actions/setup-go@v3
+        with:
+          go-version: "~1.19"
+
+      - name: Go Cache Paths
+        if: matrix.language == 'go'
+        id: go-cache-paths
+        run: |
+          echo "GOMODCACHE=$(go env GOMODCACHE)" >> $GITHUB_OUTPUT
+
+      - name: Go Mod Cache
+        if: matrix.language == 'go'
+        uses: actions/cache@v3
+        with:
+          path: ${{ steps.go-cache-paths.outputs.GOMODCACHE }}
+          key: ${{ runner.os }}-release-go-mod-${{ hashFiles('**/go.sum') }}
+
+      # Workaround to prevent CodeQL from building the dashboard.
+      - name: Remove Makefile
+        if: matrix.language == 'go'
+        run: |
+          rm Makefile
+
+      - name: Perform CodeQL Analysis
+        uses: github/codeql-action/analyze@v2
+        with:
+          category: "/language:${{matrix.language}}"
+
+  trivy:
+    name: Trivy
+    runs-on: ${{ github.repository_owner == 'coder' && 'ubuntu-latest-16-cores' || 'ubuntu-latest' }}
+    steps:
+      - uses: actions/checkout@v3
+        with:
+          fetch-depth: 0
+
+      - uses: actions/setup-go@v3
+        with:
+          go-version: "~1.19"
+
+      - name: Go Cache Paths
+        id: go-cache-paths
+        run: |
+          echo "GOMODCACHE=$(go env GOMODCACHE)" >> $GITHUB_OUTPUT
+
+      - name: Go Mod Cache
+        uses: actions/cache@v3
+        with:
+          path: ${{ steps.go-cache-paths.outputs.GOMODCACHE }}
+          key: ${{ runner.os }}-release-go-mod-${{ hashFiles('**/go.sum') }}
+
+      - name: Cache Node
+        id: cache-node
+        uses: actions/cache@v3
+        with:
+          path: |
+            **/node_modules
+            .eslintcache
+          key: js-${{ runner.os }}-test-${{ hashFiles('**/yarn.lock') }}
+          restore-keys: |
+            js-${{ runner.os }}-
+
+      - name: Build Coder linux amd64 Docker image
+        id: build
+        run: |
+          set -euo pipefail
+          image_job="build/coder_$(./scripts/version.sh)_linux_amd64.tag"
+          DOCKER_IMAGE_NO_PREREQUISITES=true make -j "$image_job"
+          echo "image=$(cat "$image_job")" >> $GITHUB_OUTPUT
+
+      - name: Run Trivy vulnerability scanner
+        uses: aquasecurity/trivy-action@7b7aa264d83dc58691451798b4d117d53d21edfe
+        with:
+          image-ref: ${{ steps.build.outputs.image }}
+          format: sarif
+          output: trivy-results.sarif
+          severity: "CRITICAL,HIGH"
+
+      - name: Upload Trivy scan results to GitHub Security tab
+        uses: github/codeql-action/upload-sarif@v2
+        with:
+          sarif_file: trivy-results.sarif
+
+      - name: Upload Trivy scan results as an artifact
+        uses: actions/upload-artifact@v2
+        with:
+          name: trivy
+          path: trivy-results.sarif
+          retention-days: 7
diff --git a/Makefile b/Makefile
index 1d10189b40..de06035632 100644
--- a/Makefile
+++ b/Makefile
@@ -92,6 +92,19 @@ CODER_FAT_NOVERSION_BINARIES      := $(addprefix build/coder_,$(OS_ARCHES))
 CODER_ALL_NOVERSION_IMAGES        := $(foreach arch, $(DOCKER_ARCHES), build/coder_linux_$(arch).tag) build/coder_linux.tag
 CODER_ALL_NOVERSION_IMAGES_PUSHED := $(addprefix push/, $(CODER_ALL_NOVERSION_IMAGES))
 
+# If callers are only building Docker images and not the packages and archives,
+# we can skip those prerequisites as they are not actually required and only
+# specified to avoid concurrent write failures.
+ifdef DOCKER_IMAGE_NO_PREREQUISITES
+CODER_ARCH_IMAGE_PREREQUISITES :=
+else
+CODER_ARCH_IMAGE_PREREQUISITES := \
+	build/coder_$(VERSION)_%.apk \
+	build/coder_$(VERSION)_%.deb \
+	build/coder_$(VERSION)_%.rpm \
+	build/coder_$(VERSION)_%.tar.gz
+endif
+
 
 clean:
 	rm -rf build site/out
@@ -296,13 +309,7 @@ $(CODER_ALL_NOVERSION_IMAGES_PUSHED): push/build/coder_%: push/build/coder_$(VER
 #
 # Images need to run after the archives and packages are built, otherwise they
 # cause errors like "file changed as we read it".
-$(CODER_ARCH_IMAGES): build/coder_$(VERSION)_%.tag: \
-	build/coder_$(VERSION)_% \
-	build/coder_$(VERSION)_%.apk \
-	build/coder_$(VERSION)_%.deb \
-	build/coder_$(VERSION)_%.rpm \
-	build/coder_$(VERSION)_%.tar.gz
-
+$(CODER_ARCH_IMAGES): build/coder_$(VERSION)_%.tag: build/coder_$(VERSION)_% $(CODER_ARCH_IMAGE_PREREQUISITES)
 	$(get-mode-os-arch-ext)
 
 	image_tag="$$(./scripts/image_tag.sh --arch "$$arch" --version "$(VERSION)")"