Unable to send large attachment in Mail

I'm trying to send a 38MB PDF file through the Mail app. I keep getting a message that says:

"Unable to send attachment with Mail Drop Try again later"


This topic was discussed in 2017, without a satisfactory answer. In using the Reunion database program, the Help advised that it was necessary to compress (zip) a large file before attaching it to Mail (or gmail) to keep special characters in the file from confusing the IP server. I tried it, and my 26 MB zip file went without a hitch. Uncompressed, it had failed multiple times.

Posted on Feb 13, 2020 8:16 PM

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Posted on Feb 13, 2020 10:55 PM

Every email provider and/or ISP imposes limits on email attachment. For instance, I use Yahoo as one of them and their max limit is 25 MB. Here are the limits for icloud:


https://support.apple.com/en-us/HT202305

4 replies

Feb 14, 2020 8:28 AM in response to babowa

I am aware of limits on sending large files. Apple's Mail Drop (if turned on) is supposed to automatically upload large attachments to iCloud and provide the addressee with a link to download the attachment. I found that when the message, "Unable to send attachment with Mail Drop - Try again later" appears, the simple solution is to zip the file before attaching it to Mail. This solution was suggested by Help in Reunion, a Mac-only database that works with large files and has obviously run into this problem before. It notes, "Some [senders] modify (or mangle) file attachments when sent.... Compressing...will prevent this damage."

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Unable to send large attachment in Mail

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