Are all messages sent thru the same mail server? Have you checked the responsive thru your VPN? Have you tried a different VPN or different endpoint in your VPN?

I have sort or a reverse issue. I use several mail accounts at different providers. When traveling, I can’t sent some messages. At different locations, it is a different service that is being refused. I have to use VPN for those mails to go out. It is not as simple as just geographical location. If I go to a different place in the same town, that is use a different internet connection, the service that failed me earlier may work just fine.

Robert

On 24 Mar 2017, at 16:20, Evan Kline wrote:

It doesn’t always happen for this account - some messages go through fine. I’ll see if I can catch a successful and failed message in the log.

Evan

On 23 Mar 2017, at 16:05, [email protected] wrote:

Date: Thu, 23 Mar 2017 15:14:57 +0100
From: "Benny Kjær Nielsen" <[email protected]>
To: "MailMate Users" <[email protected]>
Subject: Re: [MlMt] Timing out when sending messages over VPN
Message-ID: <[email protected]>
Content-Type: text/plain; charset="utf-8"; Format="flowed"

On 20 Mar 2017, at 17:56, Evan Kline wrote:

When I try to send messages while traveling and connected to a VPN, I frequently get “Connection error (Operation Timed Out)” messages.

I went into Terminal and made a change based on this thread:

https://freron.lighthouseapp.com/projects/58672/tickets/1189-mailmate-not-sending-changes-to-server

The command I entered was this:

defaults write com.freron.MailMate MmMinimumConnectionTimeout -integer
100

Unfortunately, I’m still getting timeouts. Any other suggestions?
It’s painful switching back to using Mail when I’m traveling. My
account is an Office 365 account, connecting via IMAP.

Sounds like the timeout length is not the problem. Maybe it can never
send messages when you are connected using VPN.

Unless “frequently” means that this does not always happen for this
account?

(My apologies if this has already been sent to the list - I tried
sending it over VPN a few days ago, and don’t think it went
through).

That does appear to be the case.

You can create logs for me like this:

* Open the Activity Viewer (⌥⌘0).
* Wait for an unexpected timeout to have occurred (and maybe also a
successfully sent message if this is not a persistent issue).
* Use “Help ▸ Send Server Logs”.

Thanks in advance!

--
Benny
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