diff --git a/templates/500.html b/templates/500.html
index c8507fd5ea..b6d65baeaf 100644
--- a/templates/500.html
+++ b/templates/500.html
@@ -14,27 +14,35 @@
 <div class="errorbox">
     <div class="errorcontent">
         <h1 class="lead">{{ _("Internal server error") }}</h1>
-        <p>
-            {% trans %}
-            Your Zulip chat cannot be loaded because the server is experiencing technical difficulties.
-            {% endtrans %}
-        </p>
-        <p>
-            {% trans %}
-            This page will reload automatically when service is restored.
-            {% endtrans %}
-            {% if corporate_enabled %}
+        {% if corporate_enabled %}
+            <!-- Keep in sync with web/html/5xx-cloud.html -->
+            <p>
                 {% trans %}
-                In the meantime, you can <a href="mailto:{{support_email}}">contact Zulip support</a>.
+                Something went wrong. Sorry about that! We're aware of
+                the problem and are working to fix it.
+                Zulip will load automatically once it is working again.
                 {% endtrans %}
-            {% else %}
+            </p>
+            <p>
+                {% trans status_url="https://status.zulip.com/" %}
+                Please check <a href="{{status_url}}">Zulip Cloud status</a> for
+                more information, and <a href="mailto:{{support_email}}">contact
+                Zulip support</a> with any questions.
+                {% endtrans %}
+            </p>
+        {% else %}
+            <!-- Keep in sync with web/html/5xx.html -->
+            <p>
                 {% trans %}
-                In the meantime, you can <a href="mailto:{{support_email}}">contact
-                this server's administrators</a> for support.
+                Something went wrong. Sorry about that!
+                Zulip will load automatically once it is working again.
                 {% endtrans %}
-            {% endif %}
-        </p>
-        {% if not corporate_enabled %}
+            </p>
+            <p>
+                {% trans %}
+                <a href="mailto:{{support_email}}">Contact this server's administrators</a> for support.
+                {% endtrans %}
+            </p>
             <p>
                 {% trans troubleshooting_url="https://zulip.readthedocs.io/en/latest/production/troubleshooting.html" %}
                 If you administer this server, you may want to check out the
diff --git a/web/html/5xx-cloud.html b/web/html/5xx-cloud.html
index 921e08e9d9..8929364f7e 100644
--- a/web/html/5xx-cloud.html
+++ b/web/html/5xx-cloud.html
@@ -22,10 +22,19 @@
             <img src="/static/images/errors/500art.svg" alt=""/>
             <div class="errorbox">
                 <div class="errorcontent">
+                    <!-- Keep in sync with templates/500.html -->
                     <h1 class="lead">Internal server error</h1>
-                    <p>Zulip Cloud is currently experiencing some technical difficulties. Sorry about that!</p>
-                    <p>You can check our <a href="https://status.zulip.com/">status page</a> for more information.</p>
-                    <p>The page will reload automatically soon after service is restored.</p>
+                    <p>
+                        Something went wrong. Sorry about that! We're
+                        aware of the problem and are working to fix
+                        it. Zulip will load automatically once it is
+                        working again.
+                    </p>
+                    <p>
+                        Please check <a href="https://status.zulip.com/">Zulip Cloud status</a> for
+                        more information, and <a href="mailto:support@zulip.com">contact
+                        Zulip support</a> with any questions.
+                    </p>
                 </div>
             </div>
         </div>
diff --git a/web/html/5xx.html b/web/html/5xx.html
index eb3d0fefe7..c35c27f406 100644
--- a/web/html/5xx.html
+++ b/web/html/5xx.html
@@ -22,9 +22,15 @@
             <img src="/static/images/errors/500art.svg" alt=""/>
             <div class="errorbox">
                 <div class="errorcontent">
+                    <!-- Keep in sync with templates/500.html -->
                     <h1 class="lead">Internal server error</h1>
-                    <p>This Zulip server is currently experiencing some technical difficulties. Sorry about that!</p>
-                    <p>The page will reload automatically soon after service is restored.</p>
+                    <p>
+                        Something went wrong. Sorry about that!
+                        Zulip will load automatically once it is working again.
+                    </p>
+                    <p>If you administer this server, you may want to check out the
+                        <a href="https://zulip.readthedocs.io/en/stable/production/troubleshooting.html">Zulip server troubleshooting guide</a>.
+                    </p>
                 </div>
             </div>
         </div>
diff --git a/zerver/tests/test_signup.py b/zerver/tests/test_signup.py
index fbb24cbe3d..f7447ccc14 100644
--- a/zerver/tests/test_signup.py
+++ b/zerver/tests/test_signup.py
@@ -2305,7 +2305,7 @@ class UserSignUpTest(ZulipTestCase):
         self.assertNotIn(
             "https://zulip.readthedocs.io/en/latest/subsystems/email.html", result.content.decode()
         )
-        self.assert_in_response("server is experiencing technical difficulties", result)
+        self.assert_in_response("Something went wrong. Sorry about that!", result)
         self.assertTrue(
             "ERROR:root:Failed to deliver email during user registration" in m.output[0]
         )
@@ -2354,7 +2354,7 @@ class UserSignUpTest(ZulipTestCase):
         self.assertNotIn(
             "https://zulip.readthedocs.io/en/latest/subsystems/email.html", result.content.decode()
         )
-        self.assert_in_response("server is experiencing technical difficulties", result)
+        self.assert_in_response("Something went wrong. Sorry about that!", result)
         self.assertTrue("ERROR:root:Failed to deliver email during realm creation" in m.output[0])
 
     def test_user_default_language_and_timezone(self) -> None: