TS1307 Mail Jams in Outbox, Cannot be Switched to different Outbound

Question

Having a log jam problem with mail in Mail (dumb product name).  Sending will sometimes just jam up hard. I have 8 different email accounts with 9 different outbound email servers. 8 of the outbound are SMTP and one is proprietary MS Exchange 2007.  7 of the inbound accounts are IMAP with one being proprietary MS Exchange 2007.
The log jam frequently occurs when I am switching off the corporate VPN to the internet hence the corporate MS Exchange accounts become unreachable.  I would expect the outbound email threads to see that MS Exchange is not responding and offer the redirection to a different SMTP (I have plenty). Unfortunately it just sits and spins (like a little kid calling ms-mommy!, ms-mommy!, ms-mommy!). Worse, the outbound mail system gets completely hung up and no additional email from any other account using an accessable SMTP server will go out.  And then much worse, I can open an and all of the email, attempt to redirect to an accessable and working outbound SMTP server and nothing happens.  And then to cap off the mess, Mail will not quit so I have to kill it via one of the several task manager 'gangsta style' executions.
Sum up, when mail is jammed I have tried and have not released the mail log jam by:
1) kill and relaunch mail
2) disconnect all network and let mail calmdown, then reconnect networking
3) opening each email in the outbox and manually redirecting it to a known viable SMTP server
4) moved all outbox email into a drafts mail box and then trying to send each one, once at a time, using a different SMTP outbound or different 'from' account all together
5) rebuilding the outbound mail box after any of the aformentioned actions
I have had moderate success with:
1) moving all email to a drafts email box,
1.1) then disabling the Exchange account,
1.2) then redirecting the email to new SMTP outbound server
1.3) then killing Mail if quit refuses to work (Mail I smite thee with a three finger salute!)
1.4) then relauching Mail if it needed a good smiting!
I feel that the 5 step process is not easily encorporated into my daily workflow %-).  It has been suggested that sacrificing a chicken might help but I ran out of sacrifical chickens during the days of SCSI debugging.
Based upon this and a plethora of other problems with Exchange use in Mail and via "Calendar" (dumb product name) I have come to the conclusion that Apple does not have a working solution that is compatible with MS Exchange.  Anyone disagree or know of a way to keep this log jam from happening short of Apple fixing it (not holding my breath on that one).
Last note, while I have seen this in conjunction with the use of MS Exchange as the host server, I have read elsewhere that such log jams occur on iPhone, iPad and Mac without mention of MS Exchange being involved. This suggests a general flaw in outbound mail handling in the core Mail engine (presuming it is shared between Mac OS and iOS and a rather poor multi-threading design.

Answer 1

Having a log jam problem with mail in Mail (dumb product name).  Sending will sometimes just jam up hard. I have 8 different email accounts with 9 different outbound email servers. 8 of the outbound are SMTP and one is proprietary MS Exchange 2007.  7 of the inbound accounts are IMAP with one being proprietary MS Exchange 2007.
The log jam frequently occurs when I am switching off the corporate VPN to the internet hence the corporate MS Exchange accounts become unreachable.  I would expect the outbound email threads to see that MS Exchange is not responding and offer the redirection to a different SMTP (I have plenty). Unfortunately it just sits and spins (like a little kid calling ms-mommy!, ms-mommy!, ms-mommy!). Worse, the outbound mail system gets completely hung up and no additional email from any other account using an accessable SMTP server will go out.  And then much worse, I can open an and all of the email, attempt to redirect to an accessable and working outbound SMTP server and nothing happens.  And then to cap off the mess, Mail will not quit so I have to kill it via one of the several task manager 'gangsta style' executions.
Sum up, when mail is jammed I have tried and have not released the mail log jam by:
1) kill and relaunch mail
2) disconnect all network and let mail calmdown, then reconnect networking
3) opening each email in the outbox and manually redirecting it to a known viable SMTP server
4) moved all outbox email into a drafts mail box and then trying to send each one, once at a time, using a different SMTP outbound or different 'from' account all together
5) rebuilding the outbound mail box after any of the aformentioned actions
I have had moderate success with:
1) moving all email to a drafts email box,
1.1) then disabling the Exchange account,
1.2) then redirecting the email to new SMTP outbound server
1.3) then killing Mail if quit refuses to work (Mail I smite thee with a three finger salute!)
1.4) then relauching Mail if it needed a good smiting!
I feel that the 5 step process is not easily encorporated into my daily workflow %-).  It has been suggested that sacrificing a chicken might help but I ran out of sacrifical chickens during the days of SCSI debugging.
Based upon this and a plethora of other problems with Exchange use in Mail and via "Calendar" (dumb product name) I have come to the conclusion that Apple does not have a working solution that is compatible with MS Exchange.  Anyone disagree or know of a way to keep this log jam from happening short of Apple fixing it (not holding my breath on that one).
Last note, while I have seen this in conjunction with the use of MS Exchange as the host server, I have read elsewhere that such log jams occur on iPhone, iPad and Mac without mention of MS Exchange being involved. This suggests a general flaw in outbound mail handling in the core Mail engine (presuming it is shared between Mac OS and iOS and a rather poor multi-threading design.