diff --git a/.github/workflows/tugboat-pr-closed.yml b/.github/workflows/tugboat-pr-closed.yml
new file mode 100644
index 000000000..65b661e3c
--- /dev/null
+++ b/.github/workflows/tugboat-pr-closed.yml
@@ -0,0 +1,27 @@
+name: Delete Tugboat Preview
+on:
+  pull_request:
+    types:
+      - closed
+
+jobs:
+  tugboat_delete_preview:
+    runs-on: self-hosted
+    name: Delete Tugboat Preview
+    steps:
+    - name: Restore Preview ID
+      uses: actions/cache/restore@88522ab9f39a2ea568f7027eddc7d8d8bc9d59c8 # v3.3.1
+      with:
+        path: .tugboat_preview.txt
+        key: ${{ runner.os }}-tugboat-preview-id-pr-${{ github.event.pull_request.number }}
+    - name: Set Preview ID
+      run: |
+        PREVIEW_ID=$(cat .tugboat_preview.txt)
+        echo $PREVIEW_ID
+        echo "PREVIEW_ID=$PREVIEW_ID" >> $GITHUB_ENV
+    - name: Delete Tugboat Preview
+      run: |
+        curl -H "Authorization: Bearer ${{ secrets.TUGBOAT_API_TOKEN }}" \
+          -H "Content-Type: application/json" \
+          -X DELETE \
+          https://api.tugboat.vfs.va.gov/v3/previews/${{ env.PREVIEW_ID }}
\ No newline at end of file
diff --git a/.github/workflows/tugboat-pr-opened.yml b/.github/workflows/tugboat-pr-opened.yml
index e64f352c4..606a8dac5 100644
--- a/.github/workflows/tugboat-pr-opened.yml
+++ b/.github/workflows/tugboat-pr-opened.yml
@@ -3,6 +3,7 @@ on:
   pull_request:
     types:
       - opened
+      - reopened
 
 jobs:
   tugboat_create_preview:
@@ -22,7 +23,12 @@ jobs:
       run: cat .tugboat_response.json
     - name: Extract Preview ID
       run: jq -r .preview .tugboat_response.json > .tugboat_preview.txt
-    - name: Save  Preview ID
+    - name: Delete Previous Preview ID
+      continue-on-error: true
+      run: |
+        gh extension install actions/gh-actions-cache
+        gh actions-cache delete "${{ runner.os }}-tugboat-preview-id-pr-${{ github.event.pull_request.number }}" --confirm
+    - name: Save Preview ID
       uses: actions/cache/save@88522ab9f39a2ea568f7027eddc7d8d8bc9d59c8 # v3.3.1
       with:
         path: .tugboat_preview.txt
diff --git a/.github/workflows/tugboat-pr-updated.yml b/.github/workflows/tugboat-pr-updated.yml
new file mode 100644
index 000000000..2095dfdbb
--- /dev/null
+++ b/.github/workflows/tugboat-pr-updated.yml
@@ -0,0 +1,27 @@
+name: Rebuild Tugboat Preview
+on:
+  pull_request:
+    types:
+      - synchronize
+
+jobs:
+  tugboat_rebuild_preview:
+    runs-on: self-hosted
+    name: Rebuild Tugboat Preview
+    steps:
+    - name: Restore Preview ID
+      uses: actions/cache/restore@88522ab9f39a2ea568f7027eddc7d8d8bc9d59c8 # v3.3.1
+      with:
+        path: .tugboat_preview.txt
+        key: ${{ runner.os }}-tugboat-preview-id-pr-${{ github.event.pull_request.number }}
+    - name: Set Preview ID
+      run: |
+        PREVIEW_ID=$(cat .tugboat_preview.txt)
+        echo $PREVIEW_ID
+        echo "PREVIEW_ID=$PREVIEW_ID" >> $GITHUB_ENV
+    - name: Rebuild Tugboat Preview
+      run: |
+        curl -H "Authorization: Bearer ${{ secrets.TUGBOAT_API_TOKEN }}" \
+          -H "Content-Type: application/json" \
+          -X POST \
+          https://api.tugboat.vfs.va.gov/v3/previews/${{ env.PREVIEW_ID }}/rebuild
\ No newline at end of file