Apple Mail not sending large jpegs, sending thumbnails instead with no link

I emailed another Mac user (in the next room, sadly) five jpegs, and clicked yes when the warning comes up that the files are too large, so use Maildrop.


The recipient twice (two different emails, same files received small thumbnails (100k each) with no link to Maildrop.


Does someone have to have a certain version of Apple Mail in order for the files to send correctly? I've never seen Maildrop fail before.

Mac Pro, OS X El Capitan (10.11.6)

Posted on Dec 1, 2016 4:49 PM

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6 replies

Dec 2, 2016 3:12 PM in response to Barney-15E

Thanks! I did not copy and paste the files, I selected them in the dialogue box after clicking the attachments button.


Mail clearly thought it was using MailDrop, but the recipient never got the MailDrop link, only thumbnails. It remains a mystery, and if the recipient wasn't a technophobe I'd have plenty of options to work around this, but it remains a problem I can't seem to solve.


I suspect it has something to do with the recipient's older iMac and likely older version of Mail, but I still don't understand why that would matter. Does MailDrop only work with recent versions of Mail?

Dec 2, 2016 6:15 PM in response to KevinGarnett

I suspect it has something to do with the recipient's older iMac and likely older version of Mail, but I still don't understand why that would matter. Does MailDrop only work with recent versions of Mail?

No, for the recipient, it has nothing to do with the version of Mail. It should send a link to download the files from a server, just like any other download. I didn't know about the thumbnails as babowa mentioned. Perhaps they had embedded url's.

Dec 5, 2016 10:27 AM in response to Barney-15E

That's what I thought. The recipient's emails had no embedded url's, I looked at them. Just tiny jpeg attachments. The only thing I can think of is, because of the age and slowness of the recipient's iMac, the files may have taken a very long time to download, and in the meantime showed as thumbnails. But there was no message or url included in the email, so unless that can take some time to load (after the email has been opened), then it makes no sense.

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Apple Mail not sending large jpegs, sending thumbnails instead with no link

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