When I try to send a zip file to a gmail user from Apple Mail with my iCloud address, I get the following error. My zip file is 5 MB but contains a lot of files inside the archive (that's why I zipped it so I wouldn't be sending a hundred separate files). Basically, Apple Mail treats the zip archive like it is unzipped or something like that. Does anybody know a workaround?

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  • I’m not getting a size violation error but a number of files error. – Jackson Dec 8 '18 at 16:50
  • @Jackson Please read the duplicate before dismissing it. The duplicate contains an answer for your exact question. – jksoegaard Dec 8 '18 at 19:59
  • I see I guess it is similar but Apple changed the server's error message. – Jackson Dec 8 '18 at 20:14

I found a solution. I tarred my zip archive. So I used the tar command in the terminal (tar -cf output.tar input.zip) and then emailed the tarred zip file. I guess this prevents Apple from trying to count how many files are in the zip archive.

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