topic Re: Why are test messages from Outlook 2019 being categorised as spam by talktalk in Email

Why are test messages from Outlook 2019 being categorised as spam by talktalk

surfing69 — Wed, 25 Jun 2025 17:26:37 GMT

I have added my tiscali account to Outlook 2019 and usually access my emails from there.

I have recently become aware that when I test the account settings for REMOVED FOR SECURITY@tiscali.co.uk in Outlook 2019, the test emails sent are being caught by your spam filter.

However, NO MATTER how many times I mark these emails as NOT spam on your webmail platform, they keep getting caught by your spam filter !

WHY ??!

Below are screenshots showing sequence of what happens

does anyone know why the talktalk mail server keeps categorising test emails from outlook DESPITE marking these as NOT spam on the talktalk web platform???

Re: Why are test messages from Outlook 2019 being categorised as spam by talktalk

nomfezeko-TT — Wed, 25 Jun 2025 12:04:17 GMT

Hi there @surfing69 , thank you for reaching out to us. We are so sorry you have contacted us about issues with your email services; we would like to help. Kindly let me know when you started noticing this issue.

-Fez.

Re: Why are test messages from Outlook 2019 being categorised as spam by talktalk

Billx — Wed, 25 Jun 2025 13:50:25 GMT

Hi, @surfing69

Your 4 pictures are completely unreadable. There's too much info in them. and the pictures are too small.

I have found that 'NOT Spam' just moves the email/s from Spam folder to Inbox folder.

TalkTalk needs to do a lot more work on that.

Bill

Re: Why are test messages from Outlook 2019 being categorised as spam by talktalk

surfing69 — Wed, 25 Jun 2025 14:21:00 GMT

the pictures were an optional extras - incidentally if u click on one, you can expand where everything is crustal clear

are you seriously stating that marking an email as spam on the talktalk webmail does not mark these emails as NOT spam and instead just moves the message to the Inbox? This would be really really stupid!!

Re: Why are test messages from Outlook 2019 being categorised as spam by talktalk

surfing69 — Wed, 25 Jun 2025 14:27:31 GMT

a few days ago - i thought i had an issue with my emails and so did some testing and this is what i found with my tiscali account

however according to the message from Insightful One above, he has stated that the 'Not Spam' function on the talktalk webmail platform doesn't actually work as a standard Not spam rule. Instead all it does is move the message from the spam to the Inbox folder.

If this is true, this would be VERY STUPID and will escalate to head office.

Re: Why are test messages from Outlook 2019 being categorised as spam by talktalk

nomfezeko-TT — Wed, 25 Jun 2025 14:37:31 GMT

Thank you for your response @surfing69, we are willing to help with this. I will need to run checks for you. You have reported that when you get the emails, they go to your spam folder, is that's what's happening?

-Fez.

Re: Why are test messages from Outlook 2019 being categorised as spam by talktalk

surfing69 — Wed, 25 Jun 2025 14:51:15 GMT

i would kindly suggest that you read my original email again as I believe I had provided all the necessary information without having to repeat myself.

Re: Why are test messages from Outlook 2019 being categorised as spam by talktalk

nomfezeko-TT — Wed, 25 Jun 2025 15:01:33 GMT

It sounds like you're experiencing a frustrating issue with your Tiscali email account and Outlook 2019, we are so sorry for this kind of experience, we will try our best to assist. Before we can go on with checks, please try these steps to address the problem of your test emails being marked as spam:

- Ensure that your spam filter settings are configured correctly. Sometimes, filters can be overly aggressive. Look for options to adjust the sensitivity of the spam filter.
- Add your own email address to the whitelist or safe sender list in your webmail settings. This should help prevent your emails from being marked as spam.

-Sometimes, the content of the emails can trigger spam filters. Avoid using phrases or formatting that are commonly associated with spam. Keep the emails simple and straightforward.

- Ensure that your email address or domain is not blacklisted. You can use online tools to check if your email address is on any spam blacklists.

As a temporary workaround, you might try accessing your email through a different email client or directly through the webmail interface to see if the issue is specific to Outlook. By following these steps, you should be able to improve the situation with your emails being caught in the spam filter. If you continue to have problems, please do get back to us so we can further help.

-Fez.

Re: Why are test messages from Outlook 2019 being categorised as spam by talktalk

surfing69 — Wed, 25 Jun 2025 15:22:48 GMT

Please address my query regarding what the other commentator has said i.e. ' that the 'Not Spam' function on the talktalk webmail platform doesn't actually work as a standard Not spam rule. Instead all it does is move the message from the spam to the Inbox folder.' Is this true?

Regarding your comments :

- Ensure that your spam filter settings are configured correctly. Sometimes, filters can be overly aggressive. Look for options to adjust the sensitivity of the spam filter. - THIS IS YOUR SPAM FILTER - HOW DO I ADJUST THE SENSITIVITY OF YOUR FILTER~??
- Add your own email address to the whitelist or safe sender list in your webmail settings. This should help prevent your emails from being marked as spam. WHAT ARE YOU GOING ON ABOUT? IN THIS SITUATION YOUR SPAM FILTER IS STOPPING TEST EMAILS FROM OUTLOOK NOT MY EMAIL ADDRESS,

-Sometimes, the content of the emails can trigger spam filters. Avoid using phrases or formatting that are commonly associated with spam. Keep the emails simple and straightforward. AND WHAT WOULD THESE TERMS BE THAT WOULD MARK AN EMAIL AS POTENTIAL SPAM??!

- Ensure that your email address or domain is not blacklisted. You can use online tools to check if your email address is on any spam blacklists. WHY WOULD I?? IN ANY CASE, I HAVE LEARNT FROM YEARS OF BEING WITH TISCALI AND THEN WITH TALKTALK THAT EMAILS FROM TALKTALK AND TISCALI HAVE FREQUENTLY ENDED UP ON BLACKLISTS DUE TO THEM FREQUENTLY BEING USED TO DISSEMINATE SIGNIFICANT SPAM DUE TO POOR SECURITY AT YOUR END.

I am not a novice around spam, whitelists etc. However you havent provided links to where on the talktalk webmail that i can find the whitelist

Re: Why are test messages from Outlook 2019 being categorised as spam by talktalk

Billx — Wed, 25 Jun 2025 16:42:22 GMT

Hi, @surfing69

I am using quite a large screen, and nothing in your pictures is distinguishable. I don't know why.

Clicking on one of the pictures, brings up a new picture, which looks like a mobile phone, the screen of which contains your original picture. The picture in the mobile phone looks more or less the same size as the original. Also mobile phones are narrow horizontally, so your picture does not take up the full area of the phone.

Regarding the 'NOT Spam' issue, that's what I have found. I know that TalkTalk do some sort of 'spam filtering'. I don't know what that is, or what it is supposed to do. Maybe they are using some sort of AI. But I have found nothing positive in using 'NOT Spam'.

'That would be stupid'. Well I don't disagree.

'Whitelisting' incoming email addresses might be useful.

Go to TalkTalk webmail at, https://apps.talktalk.co.uk/appsuite/

Click the Cogwheel --> Click 'All Settings' --> Scroll down until you see 'Access Lists' --> Click 'Access Lists' --> Click 'Allowlist --> Click 'Add new address' --> Type the email address in the text box --> click 'Add' --> click 'X' to exit settings.

You can add your own email address/es or others.

TalkTalk 'spam filtering' will look upon your incoming email addresses a bit more kindly.

Bill

Re: Why are test messages from Outlook 2019 being categorised as spam by talktalk

fr8ys — Wed, 25 Jun 2025 17:31:28 GMT

There were issues a while ago with older versions of Outlook.

Have you seen this page and double checked your settings are correct?

https://community.talktalk.co.uk/t5/Articles/Setting-up-Email-in-Windows-mail/ta-p/2894287?_gl=1*7prh23*_up*MQ..*_ga*NzAzMDg4MDM4LjE3NTA4NzEzMzM.*_ga_88BDJ58K51*czE3NTA4NzEzMzMkbzEkZzAkdDE3NTA4NzEzMzMkajYwJGwwJGgw#older

I'm not familiar with the Outlook test messages, but are they sent from your own domain to your own domain? If so it may just be that outlook itself is thinking it's spam as the sender and recipient are the same. It may be outlook is doing this before it hits webmail and is just being replicated in Webmail From Outlook.

Looking at the photos you have provided I see you have redacted your email address. Is though, the email address in your initial post you actual one or a dummy? In case its the actual one, I will remove it from view as a security measure.

Re: Why are test messages from Outlook 2019 being categorised as spam by talktalk

nameunknown — Wed, 25 Jun 2025 17:34:30 GMT

@Billx

I tried what you said, but get a popup stating "You can not add yourself to the Allowlist".

@surfing69

I have repeated the same test as you, but with Outlook 2007 and a TalkTalk email address with the same result as you, i.e. the test message goes to Spam.

When I replied to the message (resending it to the same account) with the title modified to 'Received this Microsoft Office Outlook Test Message', leaving the content as in the original test message, it went to the Inbox, but on replying to that with the same title, and the content as in the original test message, it went to Spam again.

My assumption is that two or more repeated messages, i.e. messages with exactly the same title and content, are flagged as spam. You would expect to have to send it many times before it is flagged as spam.

I tested this theory with a message that had the title 'This is some complete nonsense' and content 'This is some complete nonsense. I am writing just anything that comes into my head. What day is it? What time is it? Is dinner ready yet?' The first time it went to the Inbox, and the next time it went to Spam.

Allowing users to add an account to the account's Allowlist ought to resolve the issue.

As this issue is only with a message to test account settings, I doubt that it is considered a big enough issue to do something about it. For me, I don't see it as a particularly big issue. On the infrequent occasion that I run such a test, I would see that a message has landed in the Spam folder, and take a look at it.

Re: Why are test messages from Outlook 2019 being categorised as spam by talktalk

Billx — Wed, 25 Jun 2025 18:21:20 GMT

Hi @nameunknown

Yes, I slightly remember that from a previous thread.

But as you say, "Allowing users to add their own account to the account's Allowlist ought to resolve the issue."

It should definitely not regard one's own email address as spam.

There is possibly an alternative way. To do the same thing via a 'Rule'.

Bill

Re: Why are test messages from Outlook 2019 being categorised as spam by talktalk

Billx — Wed, 25 Jun 2025 18:26:22 GMT

Here is my suggestion via a Rule:

abc

Off course, I don't know the full definition of the 'Keep' command.

but again, that's up to TalkTalk to tell us.

Bill

Re: Why are test messages from Outlook 2019 being categorised as spam by talktalk

surfing69 — Wed, 25 Jun 2025 18:41:17 GMT

Ref 'Is though, the email address in your initial post you actual one or a dummy? In case its the actual one, I will remove it from view as a security measure.' I must have missed this one - thanks for spotting this error.

As far as I understand the Outlook test message is sent from my tiscali account from Outlook 2019 to my tiscali account on the TalkTalk mail server. As soon as I mark it as 'Not spam', it first appears in the Inbox of TT webmail and then my Outlook 2019 inbox.

When i click on reply i see the following which confirms that the OU test message was sent to the same domain i.e.

It is at this point that it is categorised as spam or benign.

So the question here is why is TT webmail blocking an email with my tiscali address if its sent by Outlook test facility?

When I replied to the OU test message that I received in my Outlook 2019, it fell straight into the TT webmail Inbox. When I send a test message to myself from within Outlook it falls straight into the TT Inbox.

Is it something within the internet header that TT doesn't like when its sent from this particular location??

To nameunknown

'As this issue is only with a message to test account settings, I doubt that it is considered a big enough issue to do something about it. For me, I don't see it as a particularly big issue. On the infrequent occasion that I run such a test, I would see that a message has landed in the Spam folder, and take a look at it.' - I understand what you are saying but as far as i am concerned 1. this shouldn't be happening and i need to know why and 2. if i mark it as Not Spam then the TT mail server should identify it as benign and let it through to the inbox. If the 'Not spam' facility is not working as I thought it was - then I want to know why. This is just ME .

as for whitelisting, why would i do this when i can receive messages to myself sent from Outlook to TT webmail? When I clicked on the OU test message and selected add sender to allow list - I saw MY tiscali email address . This is absurd. As mentioned above there must be something within the OU test message that the TT spam handler doesnt like.

Re: Why are test messages from Outlook 2019 being categorised as spam by talktalk

surfing69 — Wed, 25 Jun 2025 18:50:43 GMT

this is what ChatGPT said

Thanks for the clarification — you're testing a TalkTalk email account in Outlook 2019, and the Outlook test message sent to that same TalkTalk account is being marked as spam by TalkTalk's own mail server. This is actually a fairly common issue with some ISPs and webmail providers.

🔍 Why TalkTalk Marks Outlook 2019 Test Messages as Spam

Here are the most likely reasons this is happening:

🔹 1. Outlook Test Messages Look Suspicious to Spam Filters

The default Outlook test message says:

“This is an e-mail message sent automatically by Microsoft Outlook while testing the settings for your account.”

This message:

Is generic and not personalized
Lacks a subject line
Has no HTML formatting
Has no message history or reputation
Often comes from localhost or internal client IPs

These characteristics make it look like phishing bait or bot-generated spam to TalkTalk’s spam filter.

🔹 2. SPF/Authentication Issues (Even on TalkTalk Domains)

Even though you're using a TalkTalk address, the test message may be sent in a way that doesn't match what TalkTalk expects (e.g., relaying through an unexpected IP, or lacking sender authentication headers like SPF/DKIM). This happens especially if:

You're on a non-TalkTalk internet connection
You're using SMTP settings with authentication but without SSL
There’s a mismatch in your Outlook From address and the configured SMTP server

🔹 3. TalkTalk Spam Filter Sensitivity

TalkTalk’s spam filter is known to be aggressive and may not differentiate between a test message and an unsolicited mail if it doesn’t have clear context.

✅ Solutions

Here’s what you can do to work around or solve the issue:

✔️ 1. Don’t Rely on the Built-In Outlook Test Message

Instead of relying on Outlook’s automatic test message:

Complete the account setup manually
Then send yourself a real test email (e.g. “Test from Outlook setup” with a subject and some content)

This avoids triggering the spam filter as easily.

✔️ 2. Mark the Message as "Not Spam" in TalkTalk Webmail

Log in to TalkTalk Webmail
Go to the Spam/Junk folder
Select the Outlook test email
Click “Not Spam” or “Move to Inbox”

This will help train the spam filter over time.

✔️ 3. Whitelist Your Own Address

Add your own email address to your TalkTalk Safe Senders list:

Settings → Mail → Filter Rules or Safe Senders
Add your email (e.g., yourname@talktalk.net)

✔️ 4. Use Secure SMTP Settings

Double-check that you’re using the correct SMTP settings for TalkTalk with full authentication and encryption:

SMTP Server: smtp.talktalk.net
Port: 587
Encryption: STARTTLS
Authentication: Yes (your full email and password)

Would you like me to guide you through checking your current Outlook 2019 settings, or provide a safe way to test the account setup without triggering the spam filter?

Re: Why are test messages from Outlook 2019 being categorised as spam by talktalk

surfing69 — Wed, 25 Jun 2025 18:54:24 GMT

i assumed you were viewing the images on a PC. I tried viewing them on my mobile phone and found that I couldn't zoom in . So the only way of viewing these images to see the details probably requires a PC/ Laptop.

Re: Why are test messages from Outlook 2019 being categorised as spam by talktalk

nameunknown — Wed, 25 Jun 2025 19:06:39 GMT

@Billx

Rules are automatically applied to the Inbox, but not to other folders such as the Spam folder, which is where the test emails land.

Re: Why are test messages from Outlook 2019 being categorised as spam by talktalk

fr8ys — Wed, 25 Jun 2025 19:19:46 GMT

@surfing69 I looked at the photos on my phone to see you'd redacted your email address. Zoom worked ok for me.

@Billx if that's the issue, someone else had a similar problem recently and they found a phone setting needed amending to use zoom. Think it was a Galaxy they had.

Re: Why are test messages from Outlook 2019 being categorised as spam by talktalk

Billx — Wed, 25 Jun 2025 19:51:21 GMT

@nameunknown

I am aware of that, usually the operation is on the Inbox only

But I've become aware that, some commands can be made to work before the emails are split into Inbox and Spam

This is part of the whole issue, which I don't fully understand yet.

Edit: The ChatGPT certainly got the 'Use Secure SMTP Settings' correct

But it also said 'Click “Not Spam” or “Move to Inbox” ' , equating “Not Spam” with “Move to Inbox”

Bill