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I have an express install of FME Flow (2024.1) on a Azure VM and I am having troubles getting a stable connection to imap.gmail.com. 

The validation is sporadic. It will validate and be working and recieving notifications and then it will give me an error that the port or security are not correct. 

Thu-11-Jul-2024 06:04:41.318 AM : com.sun.mail.util.MailConnectException: Couldn't connect to host, port: imap.gmail.com, 993; timeout 15000;

I have enabled inbound and outbound rules over port 993 for imap.gmail.com on Azure. I am not sure what else I could be missing. 

Any help is appreciated. 

Just to add to this. I have eliminated the Network side of this issue. All the appropriate ports have been set on Azure. 

Another thing to note that when the connection to IMAP started failing when I restarted the FME Flow services it seemed to fix the issue, but my feeling is that it will only be temporary. 

So my thought is that this is a FME Flow issue and not a Network one. I submitted a ticket about this and FME Support was adamant that this was not an FME issue and needed to be worked out with our IT and that they could not help me. 

We have finally found a solution to this problem. 

In Azure for some reason if you specify a specific FQDN like smtp.gmail.com or imap.gmail.com in a Azure Firewall there will be problems with the traffic and FME will struggle to validate. 

It will validate, but it will lose connection and reconnect. 

If you set a more general rule that does not specify a specific FQDN and set a rule that allows the traffic over 587 and 993 this will improve the connection stability. 

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