diff --git a/core/frontend/src/components/version-chooser/VersionCard.vue b/core/frontend/src/components/version-chooser/VersionCard.vue
index e10c4e9a5b..f3419b283f 100644
--- a/core/frontend/src/components/version-chooser/VersionCard.vue
+++ b/core/frontend/src/components/version-chooser/VersionCard.vue
@@ -76,6 +76,18 @@
           Update to latest {{ image.tag }}
         </div>
       </v-btn>
+      <v-btn
+        v-if="settings.is_pirate_mode && current && !updateAvailable && isFromBR"
+        color="warning"
+        class="mx-2 my-1 scroll-container"
+        width="195"
+        :disabled="working"
+        @click="$emit('update-bootstrap', `bluerobotics/blueos-bootstrap:master`)"
+      >
+        <div class="scroll-text">
+          Update Bootstrap
+        </div>
+      </v-btn>
       <v-btn
         v-if="newBetaAvailable"
         color="primary"
@@ -182,6 +194,9 @@ export default Vue.extend({
     working(): boolean {
       return this.loading || this.deleting
     },
+    isFromBR(): boolean {
+      return this.image.repository === 'patrickelectric/blueos-core'
+    },
   },
   methods: {
     asTimeAgo(value: string) {
diff --git a/core/frontend/src/components/version-chooser/VersionChooser.vue b/core/frontend/src/components/version-chooser/VersionChooser.vue
index 8bd5238895..94e17a56d3 100644
--- a/core/frontend/src/components/version-chooser/VersionChooser.vue
+++ b/core/frontend/src/components/version-chooser/VersionChooser.vue
@@ -61,6 +61,7 @@
           @delete="deleteVersion"
           @apply="setVersion"
           @pull-and-apply="pullAndSetVersion"
+          @update-bootstrap="updateBootstrap"
         />
         <spinning-logo
           v-if="local_versions.loading"
@@ -433,7 +434,7 @@ export default Vue.extend({
         })
       }
     },
-    async pullAndSetVersion(args: string | string[]) {
+    async pullAndSetVersion(args: string | string[], wait = true) {
       const fullname: string = Array.isArray(args) ? args[0] : args
       // This streams the output of docker pull
       this.pull_output = 'Fetching remote image...'
@@ -461,7 +462,22 @@ export default Vue.extend({
           this.status_text = tracker.overall_status
           this.show_pull_output = true
         },
-      }).then(() => { this.waitForBackendToRestart(true) })
+      }).then(() => { this.waitForBackendToRestart(wait) })
+    },
+    async updateBootstrap(image: string) {
+      const [_, tag] = image.split(':')
+      await this.pullAndSetVersion(image, false)
+        .then(() => { this.setBootstrapVersion(tag) })
+        .then(() => { this.waitForBackendToRestart(true) })
+    },
+    async setBootstrapVersion(version: string) {
+      await back_axios({
+        method: 'post',
+        url: '/version-chooser/v1.0/bootstrap/current',
+        data: {
+          tag: version,
+        },
+      })
     },
     async setVersion(args: string | string[]) {
       const fullname: string = Array.isArray(args) ? args[0] : args