Hello Adam. Could you post a scrubbed SMTP/Delivery session for these failed attempts please? The 601 error is a generic failure and indicates something went wrong when we attempted to delivery externally. If you search your Delivery logs for that server IP you should find all sessions where your server communicated with theirs. I hope that helps!

It's all public info if you know how to look anyway. Before sending this test email.  I deleted all of the logs.  Only 3 showed back up after this email. XMPPLOG.log, delivery.log, and administrative.log.  Nothing for SMTP.

I do have 4 ports in use.  SMTP 25 as TLS, IMAP 143 as TLS, Submission Port 587 TLS and 5222 XMPP.

Thank you for your help!

15:37:47.205 [67719028] Delivery started for dm@mythicalrollers.com at 3:37:47 PM
15:37:50.209 [67719028] Added to SpamCheckQueue (1 queued; 0/30 processing)
15:37:50.209 [67719028] [SpamCheckQueue] Begin Processing.
15:37:50.209 [67719028] Blocked Sender Checks started.
15:37:50.257 [67719028] Spam Checks started.
15:37:50.257 [67719028] Spam Checks skipped: User authenticated
15:37:50.257 [67719028] Spam Checks completed.
15:37:50.257 [67719028] Removed from SpamCheckQueue (0 queued or processing)
15:37:53.223 [67719028] Added to RemoteDeliveryQueue (1 queued; 0/50 processing)
15:37:53.223 [67719028] [RemoteDeliveryQueue] Begin Processing.
15:37:53.224 [67719028] Sending remote mail for dm@mythicalrollers.com
15:37:53.226 [67719028] MxRecord count: '1' for domain 'cityofaltonil.com'
15:37:53.362 [67719028] Attempting MxRecord Host Name: 'cityofaltonil-com.mail.protection.outlook.com', preference '10', Ip Count: '2'
15:37:53.362 [67719028] Attempting to send to MxRecord 'cityofaltonil-com.mail.protection.outlook.com' ip: '104.47.64.110'
15:37:53.362 [67719028] Sending remote mail to: abishop@cityofaltonil.com
15:37:53.362 [67719028] Initiating connection to 104.47.64.110
15:37:53.362 [67719028] Connecting to 104.47.64.110:25 (Id: 1)
15:37:53.362 [67719028] Binding to local IP 104.181.50.113 (Id: 1)
15:38:13.364 [67719028] Timeout connecting to 104.47.64.110 (Id: 1)
15:38:13.364 [67719028] Previous connection attempt failed. Attempting again with primary local ip.
15:38:13.364 [67719028] Connecting to 104.47.64.110:25 (Id: 2)
15:38:33.378 [67719028] Timeout connecting to 104.47.64.110 (Id: 2)
15:38:33.378 [67719028] Connection to 104.47.64.110 failed (Id: 2)
15:38:33.378 [67719028] Attempt to ip, '104.47.64.110' success: 'False'
15:38:33.378 [67719028] Attempting to send to MxRecord 'cityofaltonil-com.mail.protection.outlook.com' ip: '104.47.65.110'
15:38:33.378 [67719028] Sending remote mail to: abishop@cityofaltonil.com
15:38:33.378 [67719028] Initiating connection to 104.47.65.110
15:38:33.378 [67719028] Connecting to 104.47.65.110:25 (Id: 3)
15:38:33.378 [67719028] Binding to local IP 104.181.50.113 (Id: 3)
15:38:53.386 [67719028] Timeout connecting to 104.47.65.110 (Id: 3)
15:38:53.386 [67719028] Previous connection attempt failed. Attempting again with primary local ip.
15:38:53.386 [67719028] Connecting to 104.47.65.110:25 (Id: 4)
15:39:13.390 [67719028] Timeout connecting to 104.47.65.110 (Id: 4)
15:39:13.390 [67719028] Connection to 104.47.65.110 failed (Id: 4)
15:39:13.390 [67719028] Attempt to ip, '104.47.65.110' success: 'False'
15:39:13.393 [67719028] Removed from RemoteDeliveryQueue (0 queued or processing)
15:40:14.689 [67719028] Added to RemoteDeliveryQueue (1 queued; 0/50 processing)
15:40:14.689 [67719028] [RemoteDeliveryQueue] Begin Processing.
15:40:14.690 [67719028] Sending remote mail for dm@mythicalrollers.com
15:40:14.692 [67719028] MxRecord count: '1' for domain 'cityofaltonil.com'
15:40:14.824 [67719028] Attempting MxRecord Host Name: 'cityofaltonil-com.mail.protection.outlook.com', preference '10', Ip Count: '2'
15:40:14.824 [67719028] Attempting to send to MxRecord 'cityofaltonil-com.mail.protection.outlook.com' ip: '104.47.65.110'
15:40:14.824 [67719028] Sending remote mail to: abishop@cityofaltonil.com
15:40:14.824 [67719028] Initiating connection to 104.47.65.110
15:40:14.824 [67719028] Connecting to 104.47.65.110:25 (Id: 1)
15:40:14.824 [67719028] Binding to local IP 104.181.50.113 (Id: 1)
15:40:34.835 [67719028] Timeout connecting to 104.47.65.110 (Id: 1)
15:40:34.835 [67719028] Previous connection attempt failed. Attempting again with primary local ip.
15:40:34.835 [67719028] Connecting to 104.47.65.110:25 (Id: 2)
15:40:54.838 [67719028] Timeout connecting to 104.47.65.110 (Id: 2)
15:40:54.838 [67719028] Connection to 104.47.65.110 failed (Id: 2)
15:40:54.838 [67719028] Attempt to ip, '104.47.65.110' success: 'False'
15:40:54.838 [67719028] Attempting to send to MxRecord 'cityofaltonil-com.mail.protection.outlook.com' ip: '104.47.64.110'
15:40:54.838 [67719028] Sending remote mail to: abishop@cityofaltonil.com
15:40:54.838 [67719028] Initiating connection to 104.47.64.110
15:40:54.838 [67719028] Connecting to 104.47.64.110:25 (Id: 3)
15:40:54.839 [67719028] Binding to local IP 104.181.50.113 (Id: 3)
15:41:14.850 [67719028] Timeout connecting to 104.47.64.110 (Id: 3)
15:41:14.850 [67719028] Previous connection attempt failed. Attempting again with primary local ip.
15:41:14.850 [67719028] Connecting to 104.47.64.110:25 (Id: 4)
15:41:34.858 [67719028] Timeout connecting to 104.47.64.110 (Id: 4)
15:41:34.858 [67719028] Connection to 104.47.64.110 failed (Id: 4)
15:41:34.858 [67719028] Attempt to ip, '104.47.64.110' success: 'False'
15:41:34.862 [67719028] Delivery for dm@mythicalrollers.com to abishop@cityofaltonil.com has bounced. Reason: Remote host said: 601 Attempted to send the message to the following IPs:
    104.47.65.110, 104.47.64.110
15:41:34.880 [67719028] DSN email written to 158967719029 with status failed to abishop@cityofaltonil.com
15:41:34.882 [67719028] Delivery for dm@mythicalrollers.com to abishop@cityofaltonil.com has completed (Bounced)
15:41:34.882 [67719028] Removed from RemoteDeliveryQueue (0 queued or processing)
15:41:35.930 [67719029] Delivery started for EMPTY (via bypass) at 3:41:35 PM
15:41:35.930 [67719029] Spool message was missing Return-Path; Also missing FROM header. If this is a system message this is normal behavior.
15:41:35.931 [67719028] Removing Spool message: Killed: False, Failed: False, Finished: True
15:41:35.931 [67719028] Delivery finished for dm@mythicalrollers.com at 3:41:35 PM    [id:158967719028]
15:41:38.942 [67719029] Added to SpamCheckQueue (1 queued; 0/30 processing)
15:41:38.942 [67719029] [SpamCheckQueue] Begin Processing.
15:41:38.943 [67719029] Blocked Sender Checks started.
15:41:38.945 [67719029] Blocked Sender Checks completed.
15:41:38.998 [67719029] Spam Checks started.
15:41:38.998 [67719029] Spam Checks skipped: User authenticated
15:41:38.998 [67719029] Spam Checks completed.
15:41:38.999 [67719029] Removed from SpamCheckQueue (0 queued or processing)
15:41:41.947 [67719029] Added to LocalDeliveryQueue (1 queued; 0/50 processing)
15:41:41.947 [67719029] [LocalDeliveryQueue] Begin Processing.
15:41:41.951 [67719029] Starting local delivery to dm@mythicalrollers.com
15:41:41.960 [67719029] Delivery for EMPTY to dm@mythicalrollers.com has completed (Delivered) Filter: None
15:41:41.960 [67719029] End delivery to dm@mythicalrollers.com (MessageID: <26b786f503f949a59ab6539cc7ad243d@cityofaltonil.com>)
15:41:41.960 [67719029] Removed from LocalDeliveryQueue (0 queued or processing)
15:41:44.957 [67719029] Removing Spool message: Killed: False, Failed: False, Finished: True
15:41:44.957 [67719029] Delivery finished for  at 3:41:44 PM    [id:158967719029]

So each and every attempt here is failing to connect out on port 25. It looks like SMTP port 25 is being blocked either by something on your server or by your ISP. Some ISPs like Cox Communications do not allow outbound port 25, so it could be something like that. 

So your thoughts are I can receive on 25 but not send?  How do I change the outbound port then?  I tried changing SMTP to 465, and I ran into the same error PLUS I could not receive.  The senders would have an authentication is required error. 

Hello,

Most ISP blocks outgoing port 25 by default to avoid their customers devices to become part of spammers botnets, If they get infected by a malware.

You should tell them you want to run.your own mail server and need it to be opened.

Kind regards

You should not change the default SMTP port to anything else than 25 as it is the port defined for inter-servers exchanges. Other ports are for SMTP clients (465, 587)