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Cannot attach documents to email in iCloud

I am suddenly unable to attach a document to my iCloud email. Started about 2 to 3 weeks ago and it is not all documents. Seems to be some Word docs and some Adobe PDFs, each from different folders on my hard drive. I have several PDFs that I need to share with others and have to go to a different email account (non-iCloud) to attach and send them. What is the problem?? And more importantly, how can I fix and/or avoid this? Thanks to all who can help.

Windows, Windows 6

Posted on Jun 12, 2023 12:46 PM

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3 replies

Jun 12, 2023 1:52 PM in response to FranBalt

Perhaps this issue and resolution I encountered yesterday is related.


I used my iCloud email address to send a 35 page PDF document (45 megabytes) via iPad (iPadOS 16.5). Doing so, I chose to invoke Mail Drop, Apple’s method for sending huge attachments.

Mail Drop limits - Apple Support


I then got an error message about iCloud’s outgoing mail server not responding. This happened repeatedly as I retried the transmission.


Then on thinking about it, it seemed very odd that I heard the swoosh sound of sending mail immediately when I sent the message, as I have Settings > Mail > Undo Send Delay set to 10 seconds. So I tried setting the value to “Off” and indeed that solved my issue!


This seems like a defect to me, and I reported it to Apple.

Cannot attach documents to email in iCloud

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