ASA IPSec VPN possible Exchange/email ssue

[S891]

We have migrated site-to-site VPN from Router to ASA. There was an issue with Exchange mail between sites and it was resolved by removing "inspect esmtp" . Now some users are reporting random search issue with the inbox. Sometimes the search result for mails in the outlook keeps trying with no response. 

I am wondering if this could also be related to VPN. This issue is random. 

Thanks

[Dinesh Moudgil]

Hello fawad-alam,

Can you please confirm the mail traffic is going over VPN tunnel or not?
In either case, whenever you face issue, try using the following capture to confirm if the packets are getting dropped on ASA:

capture asp type asp-drop all

Do "show cap asp | in x.x.x.x" and share the output.
x.x.x.x being the affected user IP or mail server IP to confirm if the ASA is dropping the traffic.

Regards,
Dinesh Moudgil

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