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I noticed that sending certain links through email do not get received by the recipient. I tried to narrow down the issue, and it seems to be on the Apple side. This does not happen with every link I try to send, but I have provided one particular link below that this happens with as an example.

Description:

I create an email and place the following link in the body of the email:

https://groundedtechs.com

The email shows as "sent", shows up in my sent folder, and no error messages are created. However, the recipient never receives the email, in neither Inbox or Junk/Spam folders. This issue only happens when sending some links through email, not every link. The issue persists if sending through iCloud Mail, iPhone Mail app, and Mac OS Mail app.

I tried the following combinations of sender/receiver account addresses, with the following results:

Sender Receiver Result
Apple Email Apple Email Fail to receive
Apple Email Google Email Fail to receive
Google Email Apple Email Successfully received
Google Email Google Email Successfully received

I'm not sure why this is. Is Apple scanning sent emails for possible spam? If so, how come I never get any notification that my email was not sent through, or was rejected?

Thanks!

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    This may be something you’ll have to open a support ticket with Apple Support. They have the ability to view mail message header info and determine what happened to your messages.
    – Allan
    Apr 15 at 0:51
  • I can reproduce your issue by doing lines 2 and 3 in your table (I have not bothered with 1 and 4) with your particular link. No issue with theguardian.com. Do as @Allan suggests.
    – Gilby
    Apr 15 at 2:48
  • If Apple is detecting as spam, then reasonable (to me) that it doesn't respond to the spammer.
    – Gilby
    Apr 15 at 2:50

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