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

[surfing69]

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???

[kanya-TT]

Hey @surfing69. That was a typo, I am sorry. I meant to find if you were still having the same issue.  Kanya

[surfing69]

unfortunately i have no idea what you mean by 'I willl need @surfing69 to confirm if they still have the same issue.' and why use the plural term 'they'? 

[kanya-TT]

Hey there, @nameunknown. Thank you for your input I willl need @surfing69 to confirm if they still have the same issue. 

Kanya

[nameunknown]

@Bill 

It's quite straightforward. If anyone requires help, they can ask for it, or use Google.

It would be great if getting the spam filter rules changed were a straightforward process. Good luck to anyone attempting to do so.

Sometimes you have to accept the way things are, and find a workaround, so that you can move on with life. 😅

[Billx]

Hi @nameunknown 

The problem is that your Visual Basic program above would look like gibberish to most Outlook users.

The original poster simply wants his legitimate incoming emails to land in the TalkTalk Inbox folder , and not be shoved into  the Spam folder.

Bill

[nameunknown]

@surfing69 

Putting code like this in Outlook Visual Basic ThisOutlookSession is the way I have fixed the issue.

Public WithEvents itms As Outlook.Items

Private Sub Application_Startup()
Set itms = Application.GetNamespace("MAPI").Folders("<put account name here>").Folders("Spam").Items
End Sub

Private Sub Application_Quit()
End Sub

Private Sub itms_ItemAdd(ByVal Item As Object)
If TypeName(Item) = "MailItem" And Item.Subject = "Microsoft Office Outlook Test Message" Then
	Item.Move Application.GetNamespace("MAPI").Folders("<put account name here>").Folders("Inbox")
End If
End Sub

[Billx]

@nameunknown 

So, it looks like ChatGPT is as smart as TalkTalk AI/Open-Exchange

Bill

[fr8ys]

@Billx sorry, I got the impression you were using a phone.

[nameunknown]

@surfing69 

None of the solutions offered by ChatGPT resolve the issue on a TalkTalk emil account

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

Many short test messages (and even some longer ones) that I sent to the sender using a TalkTalk email account went to the Spam folder.

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

It says "This will help train the spam filter over time", but is certainly not making a difference in the short term.

3. Whitelist Your Own Address

Attempting to do so results in a message stating "You cannot add yourself to the Allowlist".

4. Use Secure SMTP Settings

The suggested encryption (STARTTLS) is not available in Outlook 2007

Unsurprisingly, with all of these combinations, the test message went to the Spam folder.

port 25, encryption TLS
port 465, encryption SSL
port 587, encryption TLS

[Billx]

Hi, @fr8ys 

I am using a normal PC with a normal screen.

I am not sure which zoom you are referring to.

I do have a zoom in my extensive browser, Google Chrome,

but if I go to 150%, 200%, 300%, the images are blurred.

Other images do not have that problem.

Bill

[Billx]

@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

[fr8ys]

@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.

[nameunknown]

@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.

[surfing69]

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. 

[surfing69]

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?

[surfing69]

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. 

[Billx]

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

[Billx]

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

[nameunknown]

@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.

[fr8ys]

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*7pr...

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.