diff --git a/openedx_webhooks/views/jira.py b/openedx_webhooks/views/jira.py
index b29d5f90..1a8aaee9 100644
--- a/openedx_webhooks/views/jira.py
+++ b/openedx_webhooks/views/jira.py
@@ -28,6 +28,37 @@ def get_jira_custom_fields():
         if value["custom"]
     }
 
+# Maps JIRA status : Github label dictionary
+# TODO: should load this directly from labels.yaml so the color and name info is up to date.
+# Doesn't have the URL info but that is easily constructed.
+STATUS_LABEL_DICT = {
+    'Product Review': {
+        "url": "https://api.github.com/repos/edx/edx-platform/labels/product+review",
+        "name": "product review",
+        "color": "5319e7"
+    },
+    'Community Manager Review': {
+        "url": "https://api.github.com/repos/edx/edx-platform/labels/community+manager+review",
+        "name": "community manager review",
+        "color": "207de5"
+    },
+    'Awaiting Prioritization': {
+        'url': 'https://api.github.com/repos/edx/edx-platform/labels/awaiting+prioritization',
+        'name': 'awaiting prioritization',
+        'color': 'fad8c7'
+    },
+    'Engineering Review': {
+        "url": "https://api.github.com/repos/edx/edx-platform/labels/community+manager+review",
+        "name": "community manager review",
+        "color": "207de5"
+    },
+    'Waiting on Author': {
+        "url": "https://api.github.com/repos/edx/edx-platform/labels/waiting+on+author",
+        "name": "waiting on author",
+        "color": "0052cc"
+    },
+}
+
 
 @app.route("/jira/issue/created", methods=("POST",))
 def jira_issue_created():
@@ -137,6 +168,9 @@ def jira_issue_updated():
 
     # is the issue an open source pull request?
     if event["issue"]["fields"]["project"]["key"] != "OSPR":
+        # TODO: if the issue has just been moved from the OSPR project to a new project,
+        # change the label to "engineering review". Need to figure out if we can tell that
+        # the ticket has just moved projects.
         return "I don't care"
 
     # is there a changelog?
@@ -158,15 +192,26 @@ def jira_issue_updated():
     if not pr_repo or not pr_num:
         fail_msg = '{key} is missing "Repo" or "PR Number" fields'.format(key=issue_key)
         raise Exception(fail_msg)
+
     pr_url = "/repos/{repo}/pulls/{num}".format(repo=pr_repo, num=pr_num)
+    # Need to use the Issues API for label manipulation
+    issue_url = "/repos/{repo}/issues/{num}".format(repo=pr_repo, num=pr_num)
 
     old_status = status_changelog_items[0]["fromString"]
     new_status = status_changelog_items[0]["toString"]
 
     if new_status == "Rejected":
+        # Comment on the PR to explain to look at JIRA
+        username = github.get(issue_url)["user"]["login"]
+        comment = {
+            "body": "Hello @{username}: We are unable to continue with review of your submission "
+            "at this time. Please see the associated JIRA ticket for more explanation.".format(username=username)
+        }
+        comment_resp = github.post(issue_url + "/comments", data=json.dumps(comment))
+
         # close the pull request on Github
         close_resp = github.patch(pr_url, data=json.dumps({"state": "closed"}))
-        if not close_resp.ok:
+        if not close_resp.ok or not comment_resp.ok:
             bugsnag_context['request_headers'] = close_resp.request.headers
             bugsnag_context['request_url'] = close_resp.request.url
             bugsnag_context['request_method'] = close_resp.request.method
@@ -174,5 +219,22 @@ def jira_issue_updated():
             raise requests.exceptions.RequestException(close_resp.text)
         return "Closed PR #{num}".format(num=pr_num)
 
+    elif new_status in STATUS_LABEL_DICT:
+        # Get all the existing labels on this PR
+        label_list = github.get(issue_url)["labels"]
+
+        # Add in the new label and remove the old label
+        label_list.append(STATUS_LABEL_DICT[new_status])
+        try:
+            label_list.remove(STATUS_LABEL_DICT[old_status])
+        except ValueError:
+            print("PR {num} does not have label {old_label} to remove".format(num=pr_num, old_label=STATUS_LABEL_DICT[old_status]))
+
+        # Post the new set of labels to github
+        label_resp = github.patch(issue_url, data=json.dumps({"labels": label_list}))
+        if not label_resp.ok:
+            raise requests.exceptions.RequestException(close_resp.text)
+        return "Changed label of PR #{num} to {labels}".format(num=pr_num, labels=label_list)
+
     return "no change necessary"