What does this Warning mean? Last 10 attempts to connect to SMTP Server have failed. Retrying 50 more times before disabling.

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This error can be generated from time to time if there are any connectivity or networking issues between your own SMTP server and desk. Desk will continue to try to establish a connection until it times out. When Desk cannot establish a successful connection, it will eventually time out and disable the mailbox. 

You should feel free to log into the Desk Admin / Channels / Email / Outbound Mailboxes, and re-enable the mail box. Desk will continue to try to make the connection. 

If you see this happen often, you should reach out to your Networking group as well to investigate the reason for the connectivity problem. You'll then just need to log into desk and turn the mailbox back on again.  This issue is usually a temporary networking problem and re-enabling the mailbox in the admin fixes this and gets your emails flowing again. 

I hope this helps. Have a wonderful day!