Can't send email using Outlook

[Paul_K2]

Hi Gondola,

Long time, no speak.

ISSUE

I'm having a similar issue to NanoSea with slight differences. I'm unable to send from the laptop. Started Tue 13th Feb totally out of the blue. HP Envy 17 laptop running W11 and I'm using Outlook (New) loaded by supplier (Currys). Only purchased in Dec 2023!

ACTIONS TAKEN

After yesterday's problems, I have tried to isolate where the issue lies. I initially tried to revert to Outlook (Old) which failed to work, tried a basic repair to Outlook (no change) then a deep repair (again no change).

After the failure, I did find an email in the Hotmail inbox with the message:

It looks like we don't have permission to get email for xxxxxx@tiscali.co.uk.

Account Status:

The last successful sync was on 13/02/2024 09:52:23 UTC.

This has happened to me before on my old laptops, so went into Outlook.com (is this Windows Mail that you refer to as I don't have it on my new HP?) and retyped the Tiscali password. (Not sure I understand why it would change or why there is a sync required anyway.)

Note, since having the HP, I have never been able to drag & drop Hotmail emails into Tiscali or vice versa, which I used to be able to do. Could that be part of the issue, or is that irrelevant?

I then sent a TT webmail out which was received, and Samsung Mail on my phone seems to have sent ok tonight (awaiting confirmation of receipt). 

While the errors are a little different to NanoSea's, with a different TT code, they refer to outgoing SMTP server errors. I'm unsure also why I have 2 different Failure codes. The email app settings look correct to me and I'm receiving emails ok. I'm not sure how to change the password in Outlook's settings as there doesn't appear to be that parameter present (nor do I understand why they are linked- I would have thought Outlook.com's pwd would be the only one needed.

Please HELP...any thoughts please? 

SmtpSubmissionPermanent5XXException: 
Smtp submission failed. Server 'smtp.tiscali.co.uk' Port '587'. -->
Unexpected SMTP server response. 
Expected: 235, actual: 500, whole response: 500 5.7.0 aJsRrv1nmPjGQ Authentication Denied (TT320)
 
Failure code: cf24

AND:

SmtpSubmissionPermanent5XXException: Smtp submission failed. 
Server 'smtp.tiscali.co.uk' Port '587'. --> 
Unexpected SMTP server response. Expected: 235, actual: 500, whole response: 500 5.7.0 a1F6ruBrvj5AL Authentication Denied (TT320)
 
Failure code: 3b3e

[Gondola]

There's some confusion here.

The SSL description of settings you're quoting appear to be from Windows Mail sync options. Those should be as shown below. I'm thinking that the accounts selection is taking you to the Windows Mail software that you mentioned you'd set up on Feb 17 rather than Outlook 365.

Windows Mail : IMAP

[Paul_K2]

That was what I was expecting...

The values in the Settings route have changed correctly. Other values are there :

• Outgoing Server Requires Authentication- checked
• Use same user name and password for sending mail- checked
• Require SSL for incoming mail- checked.
• Require SSL for outgoing mail- unchecked.

MS365 fields have not changed. Guess I'll have to do that from MS 365?

Kind Regards,

PK.

[Gondola]

Ah, if you have changed via the account profile journey then the settings update should have been accepted. Sometimes you need to double check that the settings have changed.

[Paul_K2]

May have spoken too soon...

Having changed server settings as discussed, the MS 365 account Info is still set to the old values. 

Shouldn't this be immediate after closing/ starting MS365? Also got a message stating my settings were out of date when the login email arrived.

Cheers,

PK.

[Gondola]

Definitely a labour of love and my way of paying it forward to everyone that has helped me.

Perfect setup and sync as items arrive is ideal for real time working.

Yes, you'll need to set up New Outlook for Windows with the same settings. However, in that specific case there is no option to amend the server settings so you will need to Remove the account and set up afresh.

[Paul_K2]

Crikey, sounds like a labour of love. Still, I used to like helping back in my IT support days. It gives a nice feeling.

I've changed the server settings, and going ok at the moment. I've also changed the sync time to 'as items arrive'.

I presume my other email apps (Mail on Windows, Outlook (New)) will pick up the new server names, or do I need to do a similar  exercise with them?

Thanks for all your help in this.

Take care and have a good (rest of the ) weekend.

PK.

[Gondola]

No pay, no formal days off but then as a volunteer to Community I get the pleasure of offering assistance as and when I can to our lovely members.

Good to know you got the better of the navigation. Yes, a sync interval of 2 hours seems a bit long. Depends on how many messages you receive each day but I'd shorten the interval to no more than 15 minutes.

[Paul_K2]

Hi Gondola,

Thanks for your speedy reply- do you ever get a day off??

My mistake - you were correct with the Settings route; I just hadn't scrolled down far enough on the Sync Settings to see the Advanced Mailbox Settings which were hiding behind the 'Done'/ 'Cancel' Buttons...DUH!!!

The folder syncing is set to 2 hrs so that might be part of the issue, but I feel there's a bit more going on.

Thanks again,

PK.

[Gondola]

Change email sync settings is the option you would select to get to and change server host names. But if you're still barred from making those changes then Delete Account is the option to select and set up afresh using the manual setup journey. It's an IMAP account so you're only deleting locally as all folders and messages that are on the server in the online mailbox will not be affected.

If the folders created in Outlook 365 have appeared in TalkTalk webmail's online mailbox then that suggests the IMAP protocol is working as expected. Maybe in the email sync settings there's a clue as to why some folders / messages aren't synchronised as expected.

[Paul_K2]

Thanks for the info Gondola. Duly noted.

I've tried your suggested route to make the changes, but only get a 'Manage' option, which displays a window with 'user name', 'password', 'a/c name' , 'Change email sync settings' or 'Delete Account' (which I don't want to have to do).

The only way I can get to an advanced setting seems to be in MS365 itself via:

File/ then in Account Information, click to select the Tiscali Account from the drop-down list box/  then click on 'Account Settings' icon, then click on 'Server Settings'.

This then displays the current IMAP Account Settings screen which displays advanced field names for incoming and outgoing servers.

Incidentally, folders created in MS365 don't always create/populate successfully. I've looked in TT Webmail and they are in there. Not sure if this is a MS or TT issue. I've managed to manually move emails on Webmail and they have then appeared in MS365.

Weird or what?

Kind Regards,

PK.

[Gondola]

The current certificate expires in 81 days and is usually renewed in the month before expiry.

MS365 incoming and outgoing server settings changes must be carried out via the Advanced settings of a user profile.

• Select the  Windows icon bottom left side of the taskbar
• Select the  Settings cog icon
• Select Accounts
• Select  Email & Accounts and for a first time setup select Add Account and enter the settings in the table
• Or select the email account
• Select Change account or double click on the email account and select Manage

At that point on your device you ought to see the Outlook setup to enter the TalkTalk Mail server settings: NB All talktalk domains use the exact same IMAP secure settings.

[Paul_K2]

Thanks for the head-up, Gondola.

I understand what you're saying, but don't understand how to pick up the correct names when adding the Tiscali account. MS 365 didn't seem to let me have that level of detail and both in & out servers are named 'wrongly'. Ports and encryption values are correct, though.

When in the year is is the certification carried out?- if I know, then I can be prepared should something suddenly stop working.

Also, I couldn't see any documentation for changes on W11.

Kind Regards,

Paul.

[Gondola]

Just a heads up that if the host server name is imap.tiscali.co.uk instead of imap.talktalk.net or mail.talktalk.net (recommended) then incoming mail will work currently because the alternative host server names are included on the mail.talktalk.net security certificate.

This security certificate gets renewed annually. If at any future renewal TalkTalk decide to omit the legacy host server names then the email software would not connect securely. Just saying so that you know why the recommended host server name is mail.talktalk.net (incoming) and smtp.talktalk.net (outgoing) for all TalkTalk legacy domains.

[Paul_K2]

Hi Gondola,

Many thanks for your help in this matter- it now seems to be resolved.

After some investigations on my old laptop, I've started to use MS 365's Outlook. I added my Tiscali a/c using the 'advanced option' (expecting to be able to manually put in the correct server names) using my existing password.

It didn't allow me to do this, but I have successfully sent/ received emails and can drag & drop emails from 1 a/c to the other. I'm unsure what server- name parameters are specified at the moment, but at least it works.

Now that's working, I'll address the 'Mail on Windows' & 'Outlook (New)' apps and delete/add my Tiscali a/c as I only need them as a backup/alternative.

Thanks again- you're a ☀️.

[Gondola]

The TT310 error is just a rejection by the SMTP outgoing servers due to lack of authentication. Which is why you then got the TT320 error which is a result of making too many attempts at authenticating the sending.

TalkTalk Mail (all domains) should be using the smtp.talktalk.net servers using port 587 and STARTTLS connection security and authenticated with the full email address as Username and the email password and in Outlook tick the box for My outgoing server requires authentication.

On the password question, 11 characters passes the minimum required, multicase letters are mandatory plus at least one number and one approved symbol. Some symbols can cause issues with some email clients even though they'll work for webmail authentication and keyboards on different devices can produce different symbol codes for the same key. 

[Paul_K2]

Hi Gondola,

Thanks for your reply.

Regarding passwords...my password is 11 characters, and contains alpha/numerics and special characters and I managed to use it to log into TT Webmail, so guess it's ok and not falling foul of the rules? What is the limit counter set to?

Hi Gondola,

Thanks for your reply.

Regarding passwords...my password is 11 characters, and contains alpha/numerics and special characters and I managed to use it to log into TT Webmail, so guess it's ok and not falling foul of the rules? What is the limit counter set to?

Could this issue be linked to an email received from MS Outlook around the time this started, stating:

It looks like we don't have permission to get email for paul.k_2@tiscali.co.uk.

Account Status:

The last successful sync was on 13/02/2024 09:52:23 UTC.

How to Fix It...

I'm unsure why MS Hotmail needs permission to get my Tiscali email. I've had these emails before and retyped the password to what it already is and it's goes away. If you can shed light on that, I would be eternally grateful.

The other error/Description was:

SmtpSubmissionPermanent5XXException: 
Smtp submission failed. Server 'smtp.tiscali.co.uk' Port '587'. --> 
Unexpected SMTP server response. 
Expected: 235, actual: 500, whole response: 500 5.7.0 bfdKrrnKUMRSr 
Authentication Denied (TT310)
 Failure code: cf24

The difference is the character string before 'Authentication Denied', unless I've missed something.

Kind Regards, Paul.

[Gondola]

Authentication attempts are failing to associate a username (email address) with the correct password that must also pass minimum security requirements. So yes, if the password is weak or wrong then the authentication attempt will fail and add to the limit counter that will in turn, when a threshold is reached, trigger a TT320 error and a stop on sending. 

Are you sure about the TT310 error - if so what was the associated description?

[Paul_K2]

Thanks for your reply, Gondola.

Bit of confusion re: Outlook versions. Currys set up Outlook (New) which did have a toggle. After the issue, I tried to toggle back to Mail for Windows, but that didn't work and seems to have left me with non-toggleable Outlook (New).

Then, I found that Mail for Windows was available from the Start icon, so opened that and it seemed to work; I was able to send & receive from here. I think the Tiscali A/C was already added- I don't remember doing that.

By authentication attempts, are you saying that the password is incorrect? I used the same password successfully to get into TT Webmail and saw all my folders associated with my Tiscali account in Outlook (New) and My Folders, which seem to map on to the Mail for Windows.

I tried to send an email from Outlook (New) to see if it had cleared, but got TT310 message. What does TTxxx mean? Server number?

Thanks for your help with this.
Paul.

[Gondola]

The version number does indicate New Outlook for Windows is installed. But you say you've set up the tiscali account on Windows Mail that is the former mail client that New Outlook for Windows replaces. You'd either use Windows Mail or toggle to use New Outlook for Windows.

New Outlook for Windows supports IMAP accounts and if Windows Mail has also been set up for an IMAP account then both will mirror the mail messages that are online in the tiscali mailbox so you'll lose nothing that's online by removing an email account from either email software.

The error message wasn't about email settings as such it was about the excessive number of attempts to authenticate a connection. I'd recommend starting afresh with the correct settings and an upgraded password. I recommend a password of 12 - 15 characters of multicase letters and numbers and at least one approved symbol.

[Paul_K2]

Hi Gondola,

Thanks for your reply and my apologies for not getting back sooner.

Situation

• The version of Outlook I'm using is Outlook(New).Version:1.2024.207.500, and I can get into TT webmail ok, so my password is working correctly.
• I do have MS365 on the laptop, but I've not used that. I watched the Currys staff download the Outlook (new) and set up my Tiscali account, and it seemed to be ok as all folders were populated ok, and was working fine from December to 13th Feb.
• I never use Outlook.com (webmail) unless really necessary.
• I have 'found' Mail for Windows, to which I added my Tiscali account and I have managed to send an email from my Tiscali account (although I did not manage to get many of the folders re-populated).
• Looking back at my TT email from 7/9/2022 when settings were changed, the settings are wrong, as you point out. They are wrong for both IMAP and SMTP. (IMAP should be mail.talktalk.net, and SMTP should be smtp.talktalk.net)

Questions

• If the settings are wrong, how has it let me send emails for 2 months, and then suddenly stopped? Have TT tightened up on their thresholds?
• Why has IMAP not failed as it too has incorrect settings?
• To change the settings for Outlook(New), it looks like I need to REMOVE the Tiscali account, and then add it again. Is this correct, and will I lose my email data?
• Why can I send from TT Webmail and 2 Android phones?

Before I start changing things, would you be able to shed light on the questions, please?

Have a good w/e.

Kind Regards,

Paul.