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Outlook keeps asking for Password

Hi folks,

I have recently started getting a problem with MS Office Outlook 2019 continually asking me for my password when I try to send e-mails.  I enter the password but the message keeps coming back.  I receive e-mails but cannot send because of this issue.

The password that I have entered is correct and I have tried resetting and creating a new password etc. but the problem keeps occurring.  The e-mail account settings all seem to be correct.  It was working fine a few days ago, so I suspect that some sort of Windows update could have caused the issue.

I have read the previous threads on similar issues and cant find any resolution - so any help would be gratefully appreciated - It's driving me nuts!

Stu

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Re: Outlook keeps asking for Password

Hey there SCMorey / Stu,

 

Sorry to hear you're having problens with your Outlook Mail app. Can I ask whether this is the desktop version? Do you have any issues accessing your email account when using our webmail  ? When you performed a password reset, was it from the Webmail version and then Outlook? Please give us more details so we can help.

 

Thanks,

 

Lisa

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Re: Outlook keeps asking for Password

Thanks for your reply Lisa.

The problem is on desktop, I can send and receive e-mails on my phone.  I can also send and receive on the Virgin Web App.

I reset the password via the Virgin My Profile web page and then retyped it into Outlook account settings.  I have also tried to the account repair option on Outlook, but that comes back with a message that 'something went wrong'

I tried temporarily deactivating F-Secure virus protection, but that made no difference.

I checked that all the Windows 10 updates are installed and I have also reloaded/repaired my Office 2019 suite which includes Outlook 2019.

Ironically, today everything seems to be working (so far) but based on the past few days I don't have confidence that it will remain working.

any thoughts?

regards, Stu

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Re: Outlook keeps asking for Password

@SCMorey 

Can you try entering the following command into a windows command window:

curl -vs "smtps://smtp.virginmedia.com/" -u "email@address:password" 2>&1 |findstr "VM"

replace email@address with your full email address and password with your full password.  You should end up with a single line of output:

C:\Users\timdu>curl -vs "smtps://smtp.virginmedia.com/" -u "email@address:password" 2>&1 |findstr "VM"
< 535 5.7.8 Authentication Credentials Invalid (VM300)

I only want to see the line in red.

Tim

Edit - If it's all working then there's no point in doing the above, but if it does fail again, give it a try.  The VM code can be very revealing.

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Re: Outlook keeps asking for Password

Hi Tim,  I tried as you suggested.  When I put in my e-mail address and pwd nothing happens.  Here is a screenshot with my details redacted:

C:\Users\Mum & Dad>curl -vs "smtps://smtp.virginmedia.com/" -u "xxxxxxxxx@ntlworld.com:xxxxxxxxxx" 2>&1 |findstr "VM"

C:\Users\Mum & Dad>

When I added your text without changing the email address and pwd this is what happened:

C:\Users\Mum & Dad>curl -vs "smtps://smtp.virginmedia.com/" -u "email@address:password" 2>&1 |findstr "VM"
< 535 5.7.8 Authentication Credentials Invalid (VM300)

Not sure if this helps you?

Stu

 

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Re: Outlook keeps asking for Password

As stated above if you're not seeing any password errors - then the curl line will do no good as what it does is log in and then sends HELP to the server.

The reason I put the 2>&1 |findstr "VM" on the end is that people have inadvertently posted too much when posting logs in the past (although they don't realise it, the password is sent in a form that can easily be decoded).  So I wanted to make sure that ONLY the error code comes up.

As such if the password does work properly then you will see nothing.

If you have problems with Outlook again, please try the curl command while the problem exists.

Tim

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Re: Outlook keeps asking for Password

OK Thanks Tim, I will try this when the problem happens again.  Cheers

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Re: Outlook keeps asking for Password

Hi Tim, it happened again!

This time I have run the command line that you advised.  Here is the output line:

< 525 5.7.13 Authentication Denied (VM305)

Hope this helps!

Stu

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Re: Outlook keeps asking for Password

I thought that might be the case 😣

VM are rejecting the Authentication attempt because Spam has been seen coming from your home network causing you to be listed on a third party blacklist

Spamhaus' CSS

While you can get the blacklist entry removed you MUST identify and clean the source of the spam.

The spam source can be any device but typically we have seen the following devices responsible:

Amazon Firesticks with sideloaded software
Android Mobiles
PC's using Hola Free VPN (which is not really a VPN at all but a perr to peer network).

Have a read of my post here regarding a possible way of finding the device in question:

https://community.virginmedia.com/t5/Security-matters/Searching-for-Spambots-on-your-network/td-p/40...

Edit - One way of narrowing things down is to know that for the last 24 - 48 hours no spam has been seen.  So what device have you started using again today?

Tim

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Re: Outlook keeps asking for Password

Hi Tim, thanks for the comprehensive help!

I have started working through the investigation strategy.  I am using our main desk top computer and have started testing using Wireshark -  it is capturing packets form telnet "telnet smtp.blueyonder.co.uk 25".  Just checking the next step from your instructions - I am between these two...

This shows that the capture is working.  So now we can stop the capture by clicking the stop icon in the top left and then restart it by clicking the blue fin.  You'll see a message warning that the existing capture will be lost.  Select Continue without saving.

Leave the capture running for a few hours.  If there are no packets captured then we can move on to testing the rest of the network.  If packets are captured, then you've found the infected device and need to disinfect it.

After stopping the capture, should I stop the Telnet process (close the window) before restarting capture?  I have assumed that I do need to close the Telnet, so I did and so far my no packets have been detected...

Being in these crazy Covid-19 times, all my family is using computers and phones through the day, so its hard to pinpoint the device that may be affected.  I have virus checked all my family lap-tops and nothing has been detected.  I understand that Spambots can be hard to detect, so If I do end up finding packets from one of the devices, how do I eradicate it?

Sorry for all the questions, but one thing confuses me about the black-list.  If our IP address is on it, why has the e-mail problem with Virgin Media been intermittent?

Thanks for all your help so far - you have been amazing.  I will advise when I have worked through the next steps in the plan 😀

Stu

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