diff --git a/CHANGELOG.md b/CHANGELOG.md
index e709597b..f720848a 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,9 @@
 
 ## untagged
 
+- Handle Port-25 connect errors more gracefully (common with VPNs)
+  ([#552](https://github.com/chatmail/relay/pull/552))
+
 - Avoid "acmetool not found" during initial run
   ([#550](https://github.com/chatmail/relay/pull/550))
 
diff --git a/cmdeploy/src/cmdeploy/tests/online/test_0_login.py b/cmdeploy/src/cmdeploy/tests/online/test_0_login.py
index 5f4f9778..69f79f7d 100644
--- a/cmdeploy/src/cmdeploy/tests/online/test_0_login.py
+++ b/cmdeploy/src/cmdeploy/tests/online/test_0_login.py
@@ -90,8 +90,13 @@ def login_smtp_imap(smtp, imap):
 
 
 def test_no_vrfy(chatmail_config):
+    domain = chatmail_config.mail_domain
     sock = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
-    sock.connect((chatmail_config.mail_domain, 25))
+    sock.settimeout(10)
+    try:
+        sock.connect((domain, 25))
+    except socket.timeout:
+        pytest.skip(f"port 25 not reachable for {domain}")
     banner = sock.recv(1024)
     print(banner)
     sock.send(b"VRFY wrongaddress@%s\r\n" % (chatmail_config.mail_domain.encode(),))
diff --git a/cmdeploy/src/cmdeploy/tests/online/test_1_basic.py b/cmdeploy/src/cmdeploy/tests/online/test_1_basic.py
index 980d7069..fe449e0f 100644
--- a/cmdeploy/src/cmdeploy/tests/online/test_1_basic.py
+++ b/cmdeploy/src/cmdeploy/tests/online/test_1_basic.py
@@ -118,7 +118,12 @@ def test_authenticated_from(cmsetup, maildata):
 def test_reject_missing_dkim(cmsetup, maildata, from_addr):
     recipient = cmsetup.gen_users(1)[0]
     msg = maildata("encrypted.eml", from_addr=from_addr, to_addr=recipient.addr).as_string()
-    with smtplib.SMTP(cmsetup.maildomain, 25) as s:
+    try:
+        conn = smtplib.SMTP(cmsetup.maildomain, 25, timeout=10)
+    except TimeoutError:
+        pytest.skip(f"port 25 not reachable for {cmsetup.maildomain}")
+
+    with conn as s:
         with pytest.raises(smtplib.SMTPDataError, match="No valid DKIM signature"):
             s.sendmail(from_addr=from_addr, to_addrs=recipient.addr, msg=msg)