The first problem, outgoing mail with attachments not getting saved in the sent folder, is likely to be a problem with the IMAP "APPEND" routines but I am not experiencing it here. It is actually a bit complex due to the fact that we must know the exact literal size of the message before we save it. This is tricky because attachment sizes can exceed the amount of memory Hastymail has to work with so we "stream" the message and encoded attachment data to the IMAP server. This makes it harder to determine the correct literal size before hand. Being off by even 1 byte will result in the message not getting saved and in some cases can cause the IMAP connection to become unresponsive. I will dig into it and see if I can find anything.

The second problem sounds like it could be due to a limitation on POST form data, often imposed by an apache config. When an attachment is uploaded that exceeds this limit the file is not actually saved on the server so we cannot attach it.  Can you try to reproduce the problem with different size attachments and see if it might be related? I can't recall the apache directive that limits POST form sizes but I have run into this problem with a distro installed apache2 having the limit set by default.

Thanks for the feedback,
Jason