diff --git a/.circleci/config.yml b/.circleci/config.yml
index ca89773dbd..781db88a77 100644
--- a/.circleci/config.yml
+++ b/.circleci/config.yml
@@ -1192,6 +1192,17 @@ jobs:
         name: Save package cache
         paths:
         - .buildcache/packages/store
+  trigger-merge-to-ent:
+    machine:
+      image: ubuntu-2004:202107-02
+    resource_class: medium
+    working_directory: ~/boundary
+    steps:
+    - checkout
+    - run:
+        command: |
+          ./scripts/trigger-merge-to-ent
+        name: Trigger Merge to Enterprise
   openbsd_amd64_package:
     docker:
     - image: docker.mirror.hashicorp.services/circleci/buildpack-deps
@@ -1569,4 +1580,11 @@ workflows:
           branches:
             only:
             - stable-website
+  trigger-merge-to-ent:
+    jobs:
+    - trigger-merge-to-ent:
+        filters:
+          branches:
+            only:
+            - main
   version: 2
diff --git a/.circleci/config/jobs/trigger-merge-to-ent.yml b/.circleci/config/jobs/trigger-merge-to-ent.yml
new file mode 100644
index 0000000000..b976eab5c6
--- /dev/null
+++ b/.circleci/config/jobs/trigger-merge-to-ent.yml
@@ -0,0 +1,7 @@
+executor: go-machine-medium
+steps:
+- checkout
+- run:
+    name: "Trigger Merge to Enterprise"
+    command: |
+      ./scripts/trigger-merge-to-ent
diff --git a/.circleci/config/workflows/trigger-merge-to-ent.yml b/.circleci/config/workflows/trigger-merge-to-ent.yml
new file mode 100644
index 0000000000..12edc67ce7
--- /dev/null
+++ b/.circleci/config/workflows/trigger-merge-to-ent.yml
@@ -0,0 +1,6 @@
+jobs:
+  - trigger-merge-to-ent:
+      filters:
+        branches:
+          only:
+            - main
diff --git a/scripts/trigger-merge-to-ent b/scripts/trigger-merge-to-ent
new file mode 100755
index 0000000000..1a6fb7a091
--- /dev/null
+++ b/scripts/trigger-merge-to-ent
@@ -0,0 +1,17 @@
+#!/usr/bin/env bash
+
+if [[ -z "${CIRCLE_REPOSITORY_URL}" ]]; then
+    exit 0
+fi
+
+if [[ "${CIRCLE_REPOSITORY_URL}" == *"boundary-enterprise"* ]]; then
+  exit 0
+fi
+
+if [[ -z ${CIRCLE_CI_ENT_TOK} ]]; then
+  exit 0
+fi
+
+curl -u ${CIRCLE_CI_ENT_TOK}: \
+  -d 'build_parameters[CIRCLE_JOB]=merge-oss-main' \
+  https://circleci.com/api/v1.1/project/github/hashicorp/boundary-enterprise/tree/main