I then decided to see if the meraki agent should shed some light and this was the output.
client pcc23.meraki.com:993 timed out
So it trys to make an SSL connection via port 993.
Again this cannot be excluded under "Web Shield" as it only permits http(80)/https(443).
Port 993 is IMAPS (secured IMAP), so it is the mailshield, not the webshield that is causing the issue.
If you disable SSL support in the mailshield by unchecking the "Scan secured connections" checkbox
in the mailshield preferences, then it should start working.
However, this is just a workaround. To get the root of the issue, it would be necessary to find out, why
the connection timeouts. My personal guess is that the meraki error message is wrong and in fact it is
a SSL certificate issue (the meraki agent does most probably not use the system keychain) that prevents
the meraki agent from connecting.