Postbox sometimes cannot send messages with attachments
Sending messages via GMail sometimes results in a failure message. This invariably happens after the message has been delivered completely to the remote SMTP server, as the progress bar so nicely indicates. It is therefore not a connection or authentication issue, as the error message would lead you to believe ("there was a problem connecting to smtp.gmail.com, blah blah").
Given that Postbox is supposed to copy the message to the Sent folder after delivering it to the server, my guess is that it fails at this for some reason. Note that most messages are sent without problems; I suspect it only happens when the message has attachments of a certain size. The last message to fail had two 4MB PDF documents attached.
Retrying does not help. Either the message can be sent or not - retrying so far has never produced a different result. After a few tries I sent the message using GMail, which oddly enough shows all of my attempts at sending the message. In fact, it does show all of the attempts as actual sent messages, but only the one sent from the GMail interface actually reached the destination.
I can provide screenshots but am horribly busy so won't have time to do this or that to troubleshoot the problem, which is almost certainly a Postbox bug.
Given that Postbox is supposed to copy the message to the Sent folder after delivering it to the server, my guess is that it fails at this for some reason. Note that most messages are sent without problems; I suspect it only happens when the message has attachments of a certain size. The last message to fail had two 4MB PDF documents attached.
Retrying does not help. Either the message can be sent or not - retrying so far has never produced a different result. After a few tries I sent the message using GMail, which oddly enough shows all of my attempts at sending the message. In fact, it does show all of the attempts as actual sent messages, but only the one sent from the GMail interface actually reached the destination.
I can provide screenshots but am horribly busy so won't have time to do this or that to troubleshoot the problem, which is almost certainly a Postbox bug.
2
people have this problem
I have this problem, too!
Tell me when someone solves it.
The more people who report this problem, the more it gets noticed.
The more people who report this problem, the more it gets noticed.
-
Inappropriate?Hi Morten,
Make sure Postbox is not set up to copy to the sent folder for your gmail account:
Tools / Account Settings / <gmail> / Copies and Folder
[ ] Place a Copy in
should be UNCHECKED.
gmail automatically copies to the sent folder for mail sent through smtp.gmail.com.
Do you still see the problem when that is unchecked?
Cheers,
-Scott</gmail> -
Inappropriate?Unchecking the flag does not solve the problem, but does cause slightly altered behavior (see below) - I'm still getting this error when trying to send the message:

I'm using email for business purposes and need to be able to find sent messages in my Sent folder. Google seems to use a folder called Sent Mail instead, and this is not located as conveniently in the Folders tree (as it is placed below the [Gmail] folder), so I'd strongly prefer a solution that did not involve unchecking the "place a copy" setting.
Unchecking the setting has the effect that the mail is in fact sent and does show up in my inbox, however, the error is still displayed and the message is not to be found in ANY of the sent-messages folders. I did send the message to myself, but would still expect the message to appear in the Sent Mail folder. -
Inappropriate?I exeperience the same problem since a couple of days. The strange thing is that everything worked fine before and I did not change a thing in the settings since more than 2 weeks. I use the 1.1. beta.
I’m frustrated
-
Hi Sis,
Which error are you getting when sending? Is it a timeout of the gmail smtp server or is it an error copying to the sent folder?
-Scott -
Inappropriate?Hi Scott,
I got exactly the same message like morton (see above). However the problem disappeared since two days now, everything works fine, again without changing any settings... no clue what the problem is/was. Please note that I am not using gmail but fastmail. -
thanks for the update sis. Let us know if it happens again.
Loading Profile...



EMPLOYEE