583      iPhone_iPad_Mac_apple

Apple Mail deletes attachments after sending them

Hello,

I've used Apple Mail for years without any problem but recently at the company we had to change our outgoing mail settings (SMTP relay) to SendGrid's servers. Since then, emails are delivered but mysteriously any attachment disappears. I thought it had to do with SendGrid so I contacted them and they said it has nothing to do with their SMTP service. To see if they were correct I installed Thunderbird on the same machine (MacBook Pro Late 2011 running Sierra with all software up-to-date) and guess what? The same SMTP settings work perfectly with Thunderbird even with Microsoft Outlook, emails are delivered with all attachments.

After confirming the problem was with Apple Mail I started to test different settings until I found one that worked... well sort of. Turns out that only when I switch from "Rich Text" to "Plain Text" Apple Mail can send the attachments. Obviously this is a terrible solution because my signature, HTML or a simple bullet lists are gone. To make it worse when I look in the sent folder the items that were sent with attachments using "Plain Text" don't show the attachment icon even if the email was sent with an attachment, making it hard if I'm searching for something specific through my sent items.

Any ideas why this is happening and how can I fix it? Thank you in advance, I really appreciate your help.

If you put the attachments in a folder and attach the folder, does that work?

最后更新：2017-09-23 02:43:52

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