diff --git a/.github/workflows/pr-cleanup.yaml b/.github/workflows/pr-cleanup.yaml
index cb3e6429a2233..1ec7e4a73154f 100644
--- a/.github/workflows/pr-cleanup.yaml
+++ b/.github/workflows/pr-cleanup.yaml
@@ -1,7 +1,7 @@
 name: Cleanup PR deployment and image
 on:
   pull_request:
-    types: [closed]
+    types: closed
   workflow_dispatch:
     inputs:
       pr_number:
@@ -63,5 +63,11 @@ jobs:
           (
             curl -X DELETE "https://api.cloudflare.com/client/v4/zones/${{ secrets.PR_DEPLOYMENTS_ZONE_ID }}/dns_records/$record_id" \
             -H "Authorization: Bearer ${{ secrets.PR_DEPLOYMENTS_CLOUDFLARE_API_TOKEN }}" \
-            -H "Content-Type:application/json"
+            -H "Content-Type:application/json" | jq -r '.success'
           ) || echo "DNS record not found"
+
+      - name: "Delete certificate"
+        if: ${{ github.event.pull_request.merged == true }}
+        run: |
+          set -euxo pipefail
+          kuebctl delete certificate "pr${{ steps.pr_number.outputs.PR_NUMBER }}-tls" -n pr-deployment-certs || echo "certificate not found"
diff --git a/.github/workflows/pr-deploy.yaml b/.github/workflows/pr-deploy.yaml
index 7b8b3bea69bc9..3202326b919dc 100644
--- a/.github/workflows/pr-deploy.yaml
+++ b/.github/workflows/pr-deploy.yaml
@@ -1,8 +1,11 @@
-# This action will trigger when a PR is commented on with `/deploy-pr` or when the workflow is manually triggered.
+# This action will trigger when
+# 1. when the workflow is manually triggered
+# 2. ./scripts/deploy_pr.sh is run locally
+# 3. when a PR is updated
 name: Deploy PR
 on:
-  issue_comment:
-    types: [created, edited]
+  pull_request:
+    types: synchronize
   workflow_dispatch:
     inputs:
       pr_number:
@@ -29,12 +32,12 @@ permissions:
   pull-requests: write
 
 concurrency:
-  group: ${{ github.workflow }}-PR-${{ (github.event.issue.number) || (github.event.inputs.pr_number) }}
+  group: ${{ github.workflow }}-PR-${{ github.event.pull_request.number || github.event.inputs.pr_number }}
   cancel-in-progress: true
 
 jobs:
-  pr_commented:
-    if: (github.event_name == 'issue_comment' && contains(github.event.comment.body, '/deploy-pr') && (github.event.comment.author_association == 'MEMBER' || github.event.comment.author_association == 'COLLABORATOR' || github.event.comment.author_association == 'OWNER')) || github.event_name == 'workflow_dispatch'
+  get_info:
+    if: github.event_name == 'workflow_dispatch' || github.event_name == 'pull_request'
     outputs:
       PR_NUMBER: ${{ steps.pr_info.outputs.PR_NUMBER }}
       PR_TITLE: ${{ steps.pr_info.outputs.PR_TITLE }}
@@ -42,6 +45,8 @@ jobs:
       PR_BRANCH: ${{ steps.pr_info.outputs.PR_BRANCH }}
       CODER_BASE_IMAGE_TAG: ${{ steps.set_tags.outputs.CODER_BASE_IMAGE_TAG }}
       CODER_IMAGE_TAG: ${{ steps.set_tags.outputs.CODER_IMAGE_TAG }}
+      NEW: ${{ steps.check_deployment.outputs.new }}
+      BUILD: ${{ steps.filter.outputs.all_count > steps.filter.outputs.ignored_count }}
 
     runs-on: "ubuntu-latest"
     steps:
@@ -49,11 +54,7 @@ jobs:
         id: pr_info
         run: |
           set -euxo pipefail
-          if [[ ${{ github.event_name }} == "workflow_dispatch" ]]; then
-            PR_NUMBER=${{ github.event.inputs.pr_number }}
-          else
-            PR_NUMBER=${{ github.event.issue.number }}
-          fi
+          PR_NUMBER=${{ github.event.inputs.pr_number || github.event.pull_request.number }}
           PR_TITLE=$(curl -s -H "Authorization: token ${{ secrets.GITHUB_TOKEN }}" https://api.github.com/repos/coder/coder/pulls/$PR_NUMBER | jq -r '.title')
           PR_BRANCH=$(curl -s -H "Authorization: token ${{ secrets.GITHUB_TOKEN }}" https://api.github.com/repos/coder/coder/pulls/$PR_NUMBER | jq -r '.head.ref')
           echo "PR_URL=https://github.com/coder/coder/pull/$PR_NUMBER" >> $GITHUB_OUTPUT
@@ -71,28 +72,98 @@ jobs:
           CODER_BASE_IMAGE_TAG: ghcr.io/coder/coder-preview-base:pr${{ steps.pr_info.outputs.PR_NUMBER }}
           CODER_IMAGE_TAG: ghcr.io/coder/coder-preview:pr${{ steps.pr_info.outputs.PR_NUMBER }}
 
+      - name: Set up kubeconfig
+        run: |
+          set -euxo pipefail
+          mkdir -p ~/.kube
+          echo "${{ secrets.PR_DEPLOYMENTS_KUBECONFIG }}" > ~/.kube/config
+          export KUBECONFIG=~/.kube/config
+
+      - name: Check if the helm deployment already exists
+        id: check_deployment
+        run: |
+          set -euxo pipefail
+          if helm status "pr${{ steps.pr_info.outputs.PR_NUMBER }}" --namespace "pr${{ steps.pr_info.outputs.PR_NUMBER }}" > /dev/null 2>&1; then
+            echo "Deployment already exists. Skipping deployment."
+            new=false
+          else
+            echo "Deployment doesn't exist. Creating a new one."
+            new=true
+          fi
+          echo "new=$new" >> $GITHUB_OUTPUT
+
+      - name: Find Comment
+        uses: peter-evans/find-comment@v2
+        id: fc
+        with:
+          issue-number: ${{ steps.pr_info.outputs.PR_NUMBER }}
+          comment-author: "github-actions[bot]"
+          body-includes: ":rocket:"
+          direction: last
+
       - name: Comment on PR
         id: comment_id
-        if: github.event_name == 'issue_comment'
         uses: peter-evans/create-or-update-comment@v3
         with:
+          comment-id: ${{ steps.fc.outputs.comment-id }}
           issue-number: ${{ steps.pr_info.outputs.PR_NUMBER }}
+          edit-mode: replace
           body: |
+            ---
             :rocket: Deploying PR ${{ steps.pr_info.outputs.PR_NUMBER }} ...
-            :warning: This deployment will be deleted when the PR is closed.
-          reactions: "+1"
+            ---
+          reactions: eyes
+          reactions-edit-mode: replace
+
+      - name: Checkout
+        uses: actions/checkout@v3
+        with:
+          ref: ${{ steps.pr_info.outputs.PR_BRANCH }}
+          fetch-depth: 0
+
+      - name: Check changed files
+        uses: dorny/paths-filter@v2
+        id: filter
+        with:
+          filters: |
+            all:
+              - "**"
+            ignored:
+              - "docs/**"
+              - "README.md"
+              - "examples/web-server/**"
+              - "examples/monitoring/**"
+              - "examples/lima/**"
+              - ".github/**"
+              - "offlinedocs/**"
+              - ".devcontainer/**"
+              - "helm/**"
+              - "*[^g][^o][^.][^s][^u][^m]*"
+              - "*[^g][^o][^.][^m][^o][^d]*"
+              - "*[^M][^a][^k][^e][^f][^i][^l][^e]*"
+              - "scripts/**/*[^D][^o][^c][^k][^e][^r][^f][^i][^l][^e]*"
+              - "scripts/**/*[^D][^o][^c][^k][^e][^r][^f][^i][^l][^e][.][b][^a][^s][^e]*"
+
+      - name: Print number of changed files
+        run: |
+          set -euxo pipefail
+          echo "Total number of changed files: ${{ steps.filter.outputs.all_count }}"
+          echo "Number of ignored files: ${{ steps.filter.outputs.ignored_count }}"
 
   build:
-    needs: pr_commented
+    needs: get_info
     # Skips the build job if the workflow was triggered by a workflow_dispatch event and the skip_build input is set to true
     # or if the workflow was triggered by an issue_comment event and the comment body contains --skip-build
-    if: (github.event_name == 'workflow_dispatch' && github.event.inputs.skip_build == 'false') || (github.event_name == 'issue_comment' && contains(github.event.comment.body, '--skip-build') != true)
+    # alwyas run the build job if the workflow was triggered by a pull_request event
+    if: |
+      (github.event_name == 'workflow_dispatch' && github.event.inputs.skip_build == 'false') ||
+      (github.event_name == 'pull_request' && needs.get_info.outputs.NEW == 'false')
     runs-on: ${{ github.repository_owner == 'coder' && 'buildjet-8vcpu-ubuntu-2204' || 'ubuntu-latest' }}
     env:
       DOCKER_CLI_EXPERIMENTAL: "enabled"
-      CODER_IMAGE_TAG: ${{ needs.pr_commented.outputs.CODER_IMAGE_TAG }}
-      PR_NUMBER: ${{ needs.pr_commented.outputs.PR_NUMBER }}
-      PR_BRANCH: ${{ needs.pr_commented.outputs.PR_BRANCH }}
+      CODER_IMAGE_TAG: ${{ needs.get_info.outputs.CODER_IMAGE_TAG }}
+      PR_NUMBER: ${{ needs.get_info.outputs.PR_NUMBER }}
+      PR_BRANCH: ${{ needs.get_info.outputs.PR_BRANCH }}
     steps:
       - name: Checkout
         uses: actions/checkout@v3
@@ -101,15 +172,19 @@ jobs:
           fetch-depth: 0
 
       - name: Setup Node
+        if: needs.get_info.outputs.BUILD == 'true'
         uses: ./.github/actions/setup-node
 
       - name: Setup Go
+        if: needs.get_info.outputs.BUILD == 'true'
         uses: ./.github/actions/setup-go
 
       - name: Setup sqlc
+        if: needs.get_info.outputs.BUILD == 'true'
         uses: ./.github/actions/setup-sqlc
 
       - name: GHCR Login
+        if: needs.get_info.outputs.BUILD == 'true'
         uses: docker/login-action@v2
         with:
           registry: ghcr.io
@@ -117,6 +192,7 @@ jobs:
           password: ${{ secrets.GITHUB_TOKEN }}
 
       - name: Build and push Linux amd64 Docker image
+        if: needs.get_info.outputs.BUILD == 'true'
         run: |
           set -euxo pipefail
           go mod download
@@ -133,19 +209,27 @@ jobs:
             build/coder_linux_amd64
 
   deploy:
-    needs: [build, pr_commented]
+    needs: [build, get_info]
     # Run deploy job only if build job was successful or skipped
-    if: always() && (needs.build.result == 'success' || needs.build.result == 'skipped') && needs.pr_commented.result == 'success'
+    if: always() && (needs.build.result == 'success' || needs.build.result == 'skipped') && needs.get_info.result == 'success'
     runs-on: "ubuntu-latest"
     env:
-      CODER_IMAGE_TAG: ${{ needs.pr_commented.outputs.CODER_IMAGE_TAG }}
-      PR_NUMBER: ${{ needs.pr_commented.outputs.PR_NUMBER }}
-      PR_TITLE: ${{ needs.pr_commented.outputs.PR_TITLE }}
-      PR_URL: ${{ needs.pr_commented.outputs.PR_URL }}
-      PR_BRANCH: ${{ needs.pr_commented.outputs.PR_BRANCH }}
-      PR_DEPLOYMENT_ACCESS_URL: "pr${{ needs.pr_commented.outputs.PR_NUMBER }}.${{ secrets.PR_DEPLOYMENTS_DOMAIN }}"
+      CODER_IMAGE_TAG: ${{ needs.get_info.outputs.CODER_IMAGE_TAG }}
+      PR_NUMBER: ${{ needs.get_info.outputs.PR_NUMBER }}
+      PR_TITLE: ${{ needs.get_info.outputs.PR_TITLE }}
+      PR_URL: ${{ needs.get_info.outputs.PR_URL }}
+      PR_BRANCH: ${{ needs.get_info.outputs.PR_BRANCH }}
+      PR_DEPLOYMENT_ACCESS_URL: "pr${{ needs.get_info.outputs.PR_NUMBER }}.${{ secrets.PR_DEPLOYMENTS_DOMAIN }}"
     steps:
+      - name: Set up kubeconfig
+        run: |
+          set -euxo pipefail
+          mkdir -p ~/.kube
+          echo "${{ secrets.PR_DEPLOYMENTS_KUBECONFIG }}" > ~/.kube/config
+          export KUBECONFIG=~/.kube/config
+
       - name: Check if image exists
+        if: needs.get_info.outputs.NEW == 'true'
         run: |
           set -euxo pipefail
           foundTag=$(curl -fsSL https://github.com/coder/coder/pkgs/container/coder-preview | grep -o ${{ env.CODER_IMAGE_TAG }} | head -n 1)
@@ -157,27 +241,20 @@ jobs:
           fi
 
       - name: Add DNS record to Cloudflare
+        if: needs.get_info.outputs.NEW == 'true'
         run: |
-          (
-            curl -X POST "https://api.cloudflare.com/client/v4/zones/${{ secrets.PR_DEPLOYMENTS_ZONE_ID }}/dns_records" \
-          -H "Authorization: Bearer ${{ secrets.PR_DEPLOYMENTS_CLOUDFLARE_API_TOKEN }}" \
-          -H "Content-Type:application/json" \
-          --data '{"type":"CNAME","name":"*.${{ env.PR_DEPLOYMENT_ACCESS_URL }}","content":"${{ env.PR_DEPLOYMENT_ACCESS_URL }}","ttl":1,"proxied":false}'
-          )
+          curl -X POST "https://api.cloudflare.com/client/v4/zones/${{ secrets.PR_DEPLOYMENTS_ZONE_ID }}/dns_records" \
+            -H "Authorization: Bearer ${{ secrets.PR_DEPLOYMENTS_CLOUDFLARE_API_TOKEN }}" \
+            -H "Content-Type:application/json" \
+            --data '{"type":"CNAME","name":"*.${{ env.PR_DEPLOYMENT_ACCESS_URL }}","content":"${{ env.PR_DEPLOYMENT_ACCESS_URL }}","ttl":1,"proxied":false}'
 
       - name: Checkout
         uses: actions/checkout@v3
         with:
           ref: ${{ env.PR_BRANCH }}
 
-      - name: Set up kubeconfig
-        run: |
-          set -euxo pipefail
-          mkdir -p ~/.kube
-          echo "${{ secrets.PR_DEPLOYMENTS_KUBECONFIG }}" > ~/.kube/config
-          export KUBECONFIG=~/.kube/config
-
       - name: Create PR namespace
+        if: needs.get_info.outputs.NEW == 'true'
         run: |
           set -euxo pipefail
           # try to delete the namespace, but don't fail if it doesn't exist
@@ -185,6 +262,7 @@ jobs:
           kubectl create namespace "pr${{ env.PR_NUMBER }}"
 
       - name: Check and Create Certificate
+        if: needs.get_info.outputs.NEW == 'true'
         run: |
           # Using kubectl to check if a Certificate resource already exists
           # we are doing this to avoid letsenrypt rate limits
@@ -216,6 +294,7 @@ jobs:
           )
 
       - name: Set up PostgreSQL database
+        if: needs.get_info.outputs.NEW == 'true'
         run: |
           helm repo add bitnami https://charts.bitnami.com/bitnami
           helm install coder-db bitnami/postgresql \
@@ -227,28 +306,8 @@ jobs:
           kubectl create secret generic coder-db-url -n pr${{ env.PR_NUMBER }} \
             --from-literal=url="postgres://coder:coder@coder-db-postgresql.pr${{ env.PR_NUMBER }}.svc.cluster.local:5432/coder?sslmode=disable"
 
-      - name: Get experiments
-        id: get_experiments
-        run: |
-          set -euxo pipefail
-          if [[ ${{ github.event_name }} == "workflow_dispatch" ]]; then
-            experiments=${{ github.event.inputs.experiments }}
-          else
-            # extract experiments part
-            extracted_experiments=$(echo "$COMMENT_BODY" | grep -oP '(?<=--experiments )[^ ]+')
-            # Validate that the experiments is a comma-separated list of alphanumeric strings, "*", or "-"
-            if [[ $extracted_experiments =~ ^[a-zA-Z0-9_*,\"-]+$ ]]; then
-              experiments=$extracted_experiments
-            else
-              echo "Invalid input: $extracted_experiments"
-              exit 1
-            fi
-          fi
-          echo "experiments=$experiments" >> $GITHUB_OUTPUT
-        env:
-          COMMENT_BODY: ${{ github.event.comment.body || '' }}
-
       - name: Create values.yaml
+        if: github.event_name == 'workflow_dispatch'
         run: |
           cat <<EOF > pr-deploy-values.yaml
           coder:
@@ -273,7 +332,7 @@ jobs:
               - name: "CODER_WILDCARD_ACCESS_URL"
                 value: "*.${{ env.PR_DEPLOYMENT_ACCESS_URL }}"
               - name: "CODER_EXPERIMENTS"
-                value: "*,${{ steps.get_experiments.outputs.experiments }}"
+                value: "${{ github.event.inputs.experiments }}"
               - name: CODER_PG_CONNECTION_URL
                 valueFrom:
                   secretKeyRef:
@@ -289,14 +348,27 @@ jobs:
                 value: "coder"
           EOF
 
-      - name: Install Helm chart
+      - name: Install/Upgrade Helm chart
         run: |
-          helm upgrade --install "pr${{ env.PR_NUMBER }}" ./helm \
-          --namespace "pr${{ env.PR_NUMBER }}" \
-          --values ./pr-deploy-values.yaml \
-          --force
+          set -euxo pipefail
+          if [[ ${{ github.event_name }} == "workflow_dispatch" ]]; then
+            helm upgrade --install "pr${{ env.PR_NUMBER }}" ./helm \
+            --namespace "pr${{ env.PR_NUMBER }}" \
+            --values ./pr-deploy-values.yaml \
+            --force
+          else
+            if [[ ${{ needs.get_info.outputs.BUILD }} == "true" ]]; then
+              helm upgrade --install "pr${{ env.PR_NUMBER }}" ./helm \
+              --namespace "pr${{ env.PR_NUMBER }}" \
+              --reuse-values \
+              --force
+            else
+              echo "Skipping helm upgrade, as there is no new image to deploy"
+            fi
+          fi
 
       - name: Install coder-logstream-kube
+        if: needs.get_info.outputs.NEW == 'true'
         run: |
           helm repo add coder-logstream-kube https://helm.coder.com/logstream-kube
           helm upgrade --install coder-logstream-kube coder-logstream-kube/coder-logstream-kube \
@@ -304,6 +376,7 @@ jobs:
             --set url="https://pr${{ env.PR_NUMBER }}.${{ secrets.PR_DEPLOYMENTS_DOMAIN }}"
 
       - name: Get Coder binary
+        if: needs.get_info.outputs.NEW == 'true'
         run: |
           set -euxo pipefail
 
@@ -329,6 +402,7 @@ jobs:
           mv "${DEST}" /usr/local/bin/coder
 
       - name: Create first user, template and workspace
+        if: needs.get_info.outputs.NEW == 'true'
         id: setup_deployment
         run: |
           set -euxo pipefail
@@ -364,6 +438,7 @@ jobs:
           coder stop test -y
 
       - name: Send Slack notification
+        if: needs.get_info.outputs.NEW == 'true'
         run: |
           curl -s -o /dev/null -X POST -H 'Content-type: application/json' \
             -d \
@@ -382,23 +457,26 @@ jobs:
 
       - name: Find Comment
         uses: peter-evans/find-comment@v2
-        if: github.event_name == 'issue_comment'
         id: fc
         with:
           issue-number: ${{ env.PR_NUMBER }}
           comment-author: "github-actions[bot]"
-          body-includes: This deployment will be deleted when the PR is closed
+          body-includes: ":rocket:"
           direction: last
 
       - name: Comment on PR
         uses: peter-evans/create-or-update-comment@v3
-        if: github.event_name == 'issue_comment'
+        env:
+          STATUS: ${{ needs.get_info.outputs.NEW == 'true' && 'Created' || 'Updated' }}
         with:
           issue-number: ${{ env.PR_NUMBER }}
           edit-mode: replace
           comment-id: ${{ steps.fc.outputs.comment-id }}
           body: |
-            :heavy_check_mark: Deployed PR ${{ env.PR_NUMBER }} successfully.
-            :rocket: Access the deployment link [here](https://${{ env.PR_DEPLOYMENT_ACCESS_URL }}).
-            :warning: This deployment will be deleted when the PR is closed.
+            ---
+            :heavy_check_mark: PR ${{ env.PR_NUMBER }} ${{ env.STATUS }} successfully.
+            :rocket: Access the credentials [here](${{ secrets.PR_DEPLOYMENTS_SLACK_CHANNEL_URL }}).
+            ---
+            cc: @${{ github.actor }}
           reactions: rocket
+          reactions-edit-mode: replace
diff --git a/docs/CONTRIBUTING.md b/docs/CONTRIBUTING.md
index 0bdaaa5be78ff..e794828520e81 100644
--- a/docs/CONTRIBUTING.md
+++ b/docs/CONTRIBUTING.md
@@ -81,17 +81,20 @@ Use the following `make` commands and scripts in development:
 
 ### Deploying a PR
 
-You can test your changes by creating a PR deployment. A PR deployment can be triggered in two ways:
+You can test your changes by creating a PR deployment. There are two ways to do this:
 
-1. By commenting on the PR with `/deploy-pr`
-2. By running `./scripts/deploy-pr.sh`
-3. Available options
-   - `-s` or `--skip-build`, the image will not be built again, and the last image will be used.
-   - `-e EXPERIMENT1,EXPERIMENT2` or `--experiments EXPERIMENT1,EXPERIMENT2`, will enable the specified experiments.
-   - `-n` or `--dry-run` will display the context without deployment. e.g., branch name and PR number, etc.
-   - `-y` or `--yes`, will skip the CLI confirmation (only valid for the `./scripts/deploy-pr.sh`)
+1. By running `./scripts/deploy-pr.sh`
+2. By manually triggering the [`pr-deploy.yaml`](https://github.com/coder/coder/actions/workflows/pr-deploy.yaml) GitHub Action workflow
+   ![Deploy PR manually](./images/pr-deploy-manual.png)
 
-> Note: all flags can be used with both `./scripts/deploy-pr.sh` and `/deploy-pr` comment on the PR.
+#### Available options
+
+- `-s` or `--skip-build`, force prevents the build of the Docker image.(generally not needed as we are intelligently checking if the image needs to be built)
+- `-e EXPERIMENT1,EXPERIMENT2` or `--experiments EXPERIMENT1,EXPERIMENT2`, will enable the specified experiments. (defaults to `*`)
+- `-n` or `--dry-run` will display the context without deployment. e.g., branch name and PR number, etc.
+- `-y` or `--yes`, will skip the CLI confirmation prompt.
+
+> Note: PR deployment will be re-deployed automatically when the PR is updated. It will use the last values automatically for redeployment.
 
 > You need to be a member or collaborator of the of [coder](github.com/coder) GitHub organization to be able to deploy a PR.
 
diff --git a/docs/images/pr-deploy-manual.png b/docs/images/pr-deploy-manual.png
new file mode 100644
index 0000000000000..eab92cc2249e7
Binary files /dev/null and b/docs/images/pr-deploy-manual.png differ