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when reply to an email after outlook for mac has been idled, the outgoing connection to kerio connect seems to have been dropped. Thus, the email cannot be sent out.

however, if I send or reply to email right after outlook has just fetched new emails, the emails get sent without any issues.

If I close outlook and reopen, the stuck email in the last session also gets sent.

our kerio is behind a proxy server.

What ports or redirects should be setup in our apache?

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