diff --git a/CHANGELOG.md b/CHANGELOG.md
index 72679cdc..8b5f2da3 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -14,6 +14,7 @@ All notable changes to this project will be documented in this file.
 - Spike.sh integration (#402)
 - Updated Discord integration to use discord.com instead of discordapp.com
 - Add "Failure Keyword" filtering for inbound emails (#396)
+- Add support for multiple, comma-separated keywords (#396)
 
 ### Bug Fixes
 - Removing Pager Team integration, project appears to be discontinued
diff --git a/hc/api/management/commands/smtpd.py b/hc/api/management/commands/smtpd.py
index 5dfb758b..173c582d 100644
--- a/hc/api/management/commands/smtpd.py
+++ b/hc/api/management/commands/smtpd.py
@@ -12,6 +12,15 @@ RE_UUID = re.compile(
 )
 
 
+def _match(subject, keywords):
+    for s in keywords.split(","):
+        s = s.strip()
+        if s and s in subject:
+            return True
+
+    return False
+
+
 def _process_message(remote_addr, mailfrom, mailto, data):
     to_parts = mailto.split("@")
     code = to_parts[0]
@@ -33,9 +42,9 @@ def _process_message(remote_addr, mailfrom, mailto, data):
     if check.subject or check.subject_fail:
         action = "ign"
         subject = email.message_from_string(data).get("subject", "")
-        if check.subject and check.subject in subject:
+        if check.subject and _match(subject, check.subject):
             action = "success"
-        elif check.subject_fail and check.subject_fail in subject:
+        elif check.subject_fail and _match(subject, check.subject_fail):
             action = "fail"
 
     ua = "Email from %s" % mailfrom
diff --git a/hc/api/tests/test_smtpd.py b/hc/api/tests/test_smtpd.py
index ae8240d2..5d583ab3 100644
--- a/hc/api/tests/test_smtpd.py
+++ b/hc/api/tests/test_smtpd.py
@@ -74,3 +74,27 @@ class SmtpdTestCase(BaseTestCase):
         self.assertEqual(ping.scheme, "email")
         self.assertEqual(ping.ua, "Email from foo@example.org")
         self.assertEqual(ping.kind, "ign")
+
+    def test_it_handles_multiple_subject_keywords(self):
+        self.check.subject = "SUCCESS, OK"
+        self.check.save()
+
+        body = PAYLOAD_TMPL % "[OK] Backup completed"
+        _process_message("1.2.3.4", "foo@example.org", self.email, body.encode("utf8"))
+
+        ping = Ping.objects.latest("id")
+        self.assertEqual(ping.scheme, "email")
+        self.assertEqual(ping.ua, "Email from foo@example.org")
+        self.assertEqual(ping.kind, None)
+
+    def test_it_handles_multiple_subject_fail_keywords(self):
+        self.check.subject_fail = "FAIL, WARNING"
+        self.check.save()
+
+        body = PAYLOAD_TMPL % "[WARNING] Backup did not complete"
+        _process_message("1.2.3.4", "foo@example.org", self.email, body.encode("utf8"))
+
+        ping = Ping.objects.latest("id")
+        self.assertEqual(ping.scheme, "email")
+        self.assertEqual(ping.ua, "Email from foo@example.org")
+        self.assertEqual(ping.kind, "fail")
diff --git a/templates/front/details.html b/templates/front/details.html
index bc4d9c58..093dd09a 100644
--- a/templates/front/details.html
+++ b/templates/front/details.html
@@ -73,12 +73,7 @@
                 </p>
                 <code>{{ check.url }}</code>
                 <p>
-                    {% if check.subject %}
-                    Or by sending emails with "{{ check.subject }}"
-                    in the subject line to this address:
-                    {% else %}
                     Or by sending emails to this address:
-                    {% endif %}
                 </p>
                 <code>{{ check.email }}</code>
 
diff --git a/templates/front/filtering_rules_modal.html b/templates/front/filtering_rules_modal.html
index 6b51b5c9..cb6a9e6a 100644
--- a/templates/front/filtering_rules_modal.html
+++ b/templates/front/filtering_rules_modal.html
@@ -61,7 +61,7 @@
 
                     <div class="form-group">
                         <label for="update-name-input" class="col-sm-4 control-label">
-                            Success Keyword
+                            Success Keywords
                         </label>
                         <div class="col-sm-7">
                             <input
@@ -71,14 +71,14 @@
                                 {% if not check.subject and not check.subject_fail %}disabled{% endif %}
                                 class="input-name form-control filter-by-subject" />
                             <span class="help-block">
-                                If Subject contains this keyword,
-                                treat it as "success".
+                                Comma-separated list of keywords. If Subject contains
+                                any of the keywords, treat it as "success".
                             </span>
                         </div>
                     </div>
                     <div class="form-group">
                         <label for="update-name-input" class="col-sm-4 control-label">
-                            Failure Keyword
+                            Failure Keywords
                         </label>
                         <div class="col-sm-7">
                             <input
@@ -88,8 +88,8 @@
                                 {% if not check.subject and not check.subject_fail %}disabled{% endif %}
                                 class="input-name form-control filter-by-subject" />
                             <span class="help-block">
-                                If Subject contains this keyword,
-                                treat it as "failure".
+                                Comma-separated list of keywords. If Subject contains
+                                any of the keywords, treat it as "failure".
                             </span>
                         </div>
                     </div>