Vanishing emails

I’ve been using Mail.app since Mac OS X 10.3, and I never had problems with it. But in recent times, and in more than one occasion, I happened to lose messages without being able to retrieve them or understand whether they reached my correspondents or not. In both cases I had to wait for a reply to verify if the original message got to its intended destination. In both cases the message was nowhere to be found inside the application.

Case 1

This has happened more often than Case 2. Basically, after sending the message, I can’t find a copy of the message either in Mail’s Sent folder, or on the server’s. This appears to happen sporadically and erratically, and it’s something I have not been able to reproduce. It doesn’t happen with particular accounts, it doesn’t happen with a particular correspondent, the message may or may not have attachments, etc. In short, there are no apparent criteria to establish a priori whether a particular email will be regularly copied in the Sent folder once sent. It happened a few times, randomly, in a totally unpredictable way.

This, of course, is especially an issue with important work-related email. My workaround in these cases is to BCC the email to myself, but the mystery as to why the vanishing takes place remains unsolved. Mail’s Outbox folder appears to be a space that only exists during the short time frame between my hitting ‘Send’ and Mail finishing sending the message (the whoosh).

Case 2

It happened only twice, and this is probably reproducible. The circumstances were the same: I’ve finished writing an email that I have to send with one or more attachments. But instead of hitting the Attach button, I accidentally hit Send. In the rush of fixing things, I try to cancel the operation, either by clicking on the small ‘×’ icon near Mail’s activity progress bar in the bottom left corner of the interface, or by pressing the Stop red button in Mail’s activity panel. In both occasions I soon discovered that the message was sent anyway, but I couldn’t find a copy anywhere inside Mail.

It’s my belief that in cases such as this, the message should be either filed in the Sent folder, or parked in the Outbox folder (made visible). Or a copy of it should remain in the Drafts folder, just in case. In all these occasions I’ve been lucky because the message did reach my correspondents — who were always kind enough to promptly reassure me that they received it without problems. However, I can’t ignore the underlying issue: that there’s no way to tell where the email has gone. As I said, this is a serious problem with work-related communications:

  • I may write a lengthy response that never reaches my correspondent: if I find out at once, it’s a hassle to have to rewrite the contents of the response from memory. If I don’t find out at once, this surely leads to future misunderstandings (“I never got your message / estimate / invoice” or “You never wrote me explaining the project in detail”, etc.)
  • I may need a record of the whole electronic correspondence, and while an email message may reach my correspondent anyway even when it’s not filed in the Sent folder by Mail, I’d really prefer to store all the emails I’ve written during such correspondence for future reference. (e.g. “As I was telling you in my message from November 11…”, etc.)
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    All in all, I very rarely had problems with email as a communication medium, but it’s rather upsetting that in Mail.app, once a message leaves the Drafts folder, it may disappear in a vacuum for good.

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    About Riccardo Mori

    Writer. Translator. Mac consultant. Enthusiast photographer. • If you like what I write, please consider supporting my writing by purchasing my short stories, Minigrooves or by making a donation. Thank you!