topic Re: SMTP server issues with Sky email using Apple Mail on iMac in Email

SMTP server issues with Sky email using Apple Mail on iMac

woolardhome — Thu, 02 Jul 2026 18:49:24 GMT

I spent 80 minutes today on a call to sky trying to find out how to resolve SMTP outgoing mail issues in Apple Mail (since last night) only to be told they didn't know why this issue has happened and are now escalating it.

I'll include screen shots to show the errors. but it seems to be related to Mail not being able to verify the identity of the server smtp.tools.sky.com and not being able to connect to an smtp server

Every time they tried to go through the settings I had to tell them those settings weren't in Apple Mail.

Any help would be appreciated.

Screenshot 2026-07-02 at 19.42.08.pngScreenshot 2026-07-02 at 19.45.39.pngScreenshot 2026-07-02 at 19.48.17.png

Re: SMTP server issues with Sky email using Apple Mail on iMac

caesarome — Thu, 02 Jul 2026 18:55:25 GMT

@woolardhome

What SMTP server settings are you using as this is what it should be:

Server - smtp.tools.sky.com
Port - 465
Requires SSL - Yes
Requires authentication - Yes

Re: SMTP server issues with Sky email using Apple Mail on iMac

woolardhome — Thu, 02 Jul 2026 19:07:07 GMT

Hi.

That's the issue. There doesn't seem to be anywhere for me to input this info. And everything was working up until last night.

Re: SMTP server issues with Sky email using Apple Mail on iMac

caesarome — Thu, 02 Jul 2026 19:14:05 GMT

What Apple device are you using ?

Re: SMTP server issues with Sky email using Apple Mail on iMac

woolardhome — Thu, 02 Jul 2026 19:19:37 GMT

iMac 2017

Ventura 13.7.8

Re: SMTP server issues with Sky email using Apple Mail on iMac

caesarome — Thu, 02 Jul 2026 19:22:41 GMT

@woolardhome

Give this a try:

Open the built-in Mail app, click Mail > Settings (or Preferences on older macOS versions), select Accounts, and click the Server Settings tab. Uncheck "Automatically manage connection settings" to edit your IMAP/POP and SMTP ports

Re: SMTP server issues with Sky email using Apple Mail on iMac

woolardhome — Thu, 02 Jul 2026 19:35:13 GMT

Screenshot 2026-07-02 at 20.34.48.png

Re: SMTP server issues with Sky email using Apple Mail on iMac

woolardhome — Thu, 02 Jul 2026 19:37:25 GMT

and still no luck I'm afraid : (

Re: SMTP server issues with Sky email using Apple Mail on iMac

jayach — Thu, 02 Jul 2026 21:21:05 GMT

Try using smtp.mail.yahoo.com and what are the other options for Authentication, as that doesn't look right. (but I'm not an Apple person)

Are you receiving email O.K. and what are the settings for IMAP server?

Re: SMTP server issues with Sky email using Apple Mail on iMac

jayach — Thu, 02 Jul 2026 22:21:07 GMT

Oh, and do you remember how you set it up? Did you use your Sky password or a generated password?

Re: SMTP server issues with Sky email using Apple Mail on iMac

James485 — Fri, 03 Jul 2026 08:52:59 GMT

Given the age of the mac are you able to check the apple keychain to see if the mentioned root certificate is missing. This would normally be available on Mac Updates.

Open Keychain Access --> System Roots -->

Screenshot 2026-07-03 at 09.48.52.png