Apple Mail does not send mail: Connection to the outgoing mail server failed

Speedport refuses Apple Mail to send emails via

Somehow the problems readers have with Apple Mail are increasing. In this case, Telekom's Speedport W 724V refused to send it via Apple's own iCloud server. The error message the reader received from Apple Mail went something like this:

Connection to outgoing mail server failed. Other outgoing email servers can be found at…

Background: iCloud server not in the whitelist of the speed port

Why is there this error? Because the Speedport routers do not allow any mail server to send e-mails in order to avoid email spam. The Speedport W 724V has a whitelist for this purpose - i.e. a list of approved mail servers. Since the iCloud servers are not stored there by default, the router blocks the sending of e-mails.

It is possible that Telekom has now inserted the Apple server into the speed ports of its own accord in order to avoid such problems, but in this case the whitelist was not yet adjusted accordingly.

Here is another screenshot that I found at Telekom. This shows where to find the list of secure mail servers.
Here is another screenshot that I took with the Telekom have found. This shows where to find the list of secure mail servers.

Instructions: Add the iCloud server to the whitelist

In order to allow the sending of your own iCloud e-mail, you have to add the wildcard subdomain * in the Speedport administration. How this works, I describe here:

  1. This address is called up from the browser in the home WLAN: http://speedport.ip
  2. In the menu on the left, go to “List of Safe E-mail Servers”.
  3. Now you can either disable the list completely (uncheck "Use list of safe email servers") or add an entry with this content: *

Now you can try sending via Apple Mail again. It should actually work now!

My tips & tricks about technology & Apple

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4 Responses to “Apple Mail not sending mail: Failed to connect to outgoing mail server”

  1. Beatrice Willius

    Gr…. I've already had this wonderful problem. When setting up the speed port, I set up everything nicely.

    Then I wanted an SSL certificate for my website for the equally wonderful data protection regulation. My host said I should switch hosting to Plesk. Then I could use Let's Encrypt. Everything worked out too. The only thing I couldn't send any more emails was because I had forgotten the speed port of course. With the Plesk hosting, the base domain also changed.

    1. Hello Beatrix! Thanks for your comment! Does that mean that if I want to send an email to my domain @ via the speed port, I also have to enter this in the list in the speed port ??? That is mega-cumbersome ...

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