Can’t send Outlook emails from my Mac

[RogerWood]

I have a Tiscali email address. On my Mac I use both Apple mail and Outlook to send messages. Apple mail works fine but as from about 10 days ago Outlook messages were not sent and generated error message 3253 “The connection to the server failed or was dropped”. I had not changed any account settings and updating Outlook from the 2016 version to 2023 has made no difference. I have not been able to find any relevant advice elsewhere online - can anyone help please? 

[Gondola]

Perfect. Just like magic! You're very welcome.

If all is OK now, to close this topic as Answered please scroll to my reply message 6 of 9, select the triple dots menu bottom right of that post and select the menu item Accept as Solution. That'll help TalkTalk Support to see no further action is required.

[RogerWood]

Hi Gondola

As suggested I changed to the talktalk.net servers with the recommended ports and set the. authentication to username and password - hey presto: normal service resumed!

Thanks for your guidance - much appreciated.

Best wishes - Roger Wood

[Gondola]

Let us know that you're back in action using Outlook for Mac 16.7

[Gondola]

Yes, use the talktalk.net servers and that applies to all TalkTalk Mail domains including tiscali.co.uk, lineone.net, onetel.com etc

Authentication is best if you use Username (the full email address) and Password (the email password).

[RogerWood]

Hi Gondola

Does that mean that I have to use these talktalk.net servers even though I have a Tiscali email address?

Under "More options" I am offered two "Authentication" choices: "Use incoming server" (current) or "Username and password".

Under "Advanced" there are two tabs "Server" and "Security"

"Server" has tick boxes for: 

- "Leave a copy of each message on server" - selected;

- "Delete copies from the server" - Selected "After deleting from this computer";

- "Download headers only" - not selected;

- "Send and receive every X minutes" - not selected.

"Server" has two sections:

- "Digital signing" "Certificate: none selected"

- "Encryption" "Certificate: none selected" & "Encryption algorithm" "AES-256 (more secure)" plus "Encrypt outgoing messages" - unchecked.

You mention: My outgoing SMTP server requires authentication.

I don't see this as a specific option but perhaps it is covered by what I have entered above?

Thanks - fingers crossed!

[Gondola]

The incoming server should be: mail.talktalk.net   PORT 995

The outgoing server should be: smtp.talktalk.net  PORT 587 (if necessary override default port)

What More options / Advanced settings are there to set up?

Usually needs My outgoing SMTP server requires authentication

[RogerWood]

Hi Gondola - thanks for your reply. 

My Mac uses macOS Big Sur version 11.7.4

My Outlook for Mac is version 16.70 (2023)

Here is a screen shot of my Outlook account settings page

 I hope this gives you enough information to restore access! thanks.

[Gondola]

You'll need to update the server settings for Outlook. Probably still using port 25 for outgoing mail. Port 25 is now blocked.

If you saw the message from TalkTalk advising "Our records show that you are still accessing your email using unencrypted email settings..." then the email address receiving that notification has now been limited to webmail only access OR has a stop on sending mail as a last resort action by TalkTalk to stop the use of email connections not secured by TLS 1.2 encryption.

TalkTalk Mail webmail is secure by design when using an up to date Internet browser.

Select here:  Sign in to TalkTalk Mail

Enter your full TalkTalk Mail email address and password, select Sign in.

A stop on sending is easily resolved by using currently supported email software and secure email settings as shown in the Email Settings guide below.

If your mailbox is limited to webmail only access for both sending and receiving mail, you will be able to get access restored to email apps or email software, including mail collection services, passwords will then re-authenticate, so long as you're ready to use supported email software and secure email settings for all the ways you view emails.

We can advise on device and software compatibility with TLS 1.2 encryption and provide customer setup guides. Just let us know each mail collection service, each device, its operating system and email software including version that are in current use.

For a definitive check of email settings take screenshots of the incoming and outgoing server settings, image edit to obscure the first part of the email address and upload here using the Camera icon (desktop browser) or Picture icon (mobile browser) above this reply area.

When you confirm the secure settings are ready I can request TalkTalk Support to restore full access. TalkTalk Support will respond here and access will be restored usually within a couple of working days.

Prepare for TalkTalk Support - include in the Community Profile (not in these public posts):

 Email account holder name

 Scroll down to Private notes to add the email address(es)
and TalkTalk or MailPlus customer account number

 Check and Save changes

Select here:  Update your profile

The TalkTalk Mail Support Hub is your go to resource for information, guides and Community support for TalkTalk Consumer home broadband and MailPlus subscribers.

Select here:
 TalkTalk Mail Support

TalkTalk Mail help
 Using TalkTalk Mail

 Email settings and device setup guides for TalkTalk Mail

 About TalkTalk Mail Plus