Emails outgoing not working

Question

Emails outgoing not working

Reinhart Evelein 0

My email is [Moderator note: PII removed] @shaw.ca. After the last update on Windows 10, I am unable to send out emails.

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3 answers

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Answer 1

Bulldog 4,625

"My regular email app (Windows Live Mail) still doesn't send mail."

Support for Windows Live Mail ended on January 10, 2017. It's not against the law to continue to use the software, but there are no official solutions for problems anyone has with the app, and no security updates either. I hope you find a solution, but nothing is guaranteed.

Reinhart Evelein 0 Reputation points

2026-06-20T14:53:42.42+00:00

Yet for some reason, I'm still getting updates.
Bulldog 4,625 Reputation points

2026-06-21T02:13:09.9466667+00:00

The final update for Windows Live Mail (to version 16.4.3528.0331) was released on April 17, 2014. Since then there have been no updates or security fixes.
Reinhart Evelein 0 Reputation points

2026-06-21T13:40:58.7666667+00:00

Well, you might be talking about a major "upgrade" for Live mail, but I get Windows "updates" for Windows 10 (and they are called "updates" by Window) every 4 days to 3 weeks. These might be security related or fix little bugs, but they certainly happen and two "updates" ago, my outgoing mail no longer functioned.

Is there anyone else who understands how Windows 10 updated might screw up my Live Mail outgoing mail?
Bulldog 4,625 Reputation points

2026-06-21T15:43:16.32+00:00

Windows 10 only receives security updates, which would not affect Windows Live Mail since it was always separate from Windows.

The good news is that you can upgrade from Windows Live Mail to Outlook.com (which is free) and be in supported software which is regularly updated (also for free).
Reinhart Evelein 0 Reputation points

2026-06-21T17:43:52.89+00:00

I'm aware of all of that and have Outlook downloaded and operating correctly with my Shaw email account. The reason I was staying with Live Mail is: I have a number of folders in Live Mail with important emails that I want to keep and I believe I cannot migrate them to Outlook, unless you know of a way to do that.

Live Mail is simpler and easy to use and, since Sin-D did determine, below, that my outgoing mail problem was related to a windows upgrade, I was hoping to be able to stay with Live Mail.
Anonymous

2026-06-21T23:21:26.77+00:00

Hi Reinhart Evelein,

I completely understand why you'd prefer to stay with Windows Live Mail. If it has years of archived emails organized into folders, switching clients can feel like a major disruption.

One thing I want to clarify: while the issue surfaced after a Windows update, I cannot definitively conclude that Windows caused it. What I can say is that the update appears to have exposed a compatibility issue affecting Windows Live Mail's ability to send mail.

Regarding your concern about your folders:

You do not necessarily have to lose your archived emails if you move away from Windows Live Mail. Many users have successfully migrated mail from Windows Live Mail to Outlook by exporting/importing messages. Before we go down that path, though, I'd like to confirm one thing:

When you say Outlook is already downloaded and operating correctly with your Shaw account, can you confirm whether Outlook is able to both receive and send emails successfully using that same account?
Bulldog 4,625 Reputation points

2026-06-22T01:50:23.29+00:00

"What I can say is that the update appears to have exposed a compatibility issue affecting Windows Live Mail's ability to send mail."

Please explain this compatibility issue. What in particular is not compatible with Windows Live Update, and how does it affect the ability to send mail?
Anonymous

2026-06-23T03:22:24.8+00:00

Hi Bulldog,

You’re right to ask for clarification. I should word that more carefully.

Based on the tests so far, I cannot confirm that a specific Windows update component is incompatible with Windows Live Mail. What we have confirmed is that the issue is isolated to Windows Live Mail, because Shaw/Rogers account can send successfully through Webmail and Outlook, but not through Windows Live Mail.

Since Windows Live Mail is an end-of-service product, it may not handle newer Windows, security, or mail-server changes as reliably as supported mail apps.

Thanks for pointing that out.
Reinhart Evelein 0 Reputation points

2026-06-23T16:58:03.5966667+00:00

I think what I should do now, after all this, is use Outlook for emails. I'm usually one who will always incorporate every update or app change (Live Mail to Outlook), because the update or new app usually provides new security and the app is better (usually, but not always). It was only because I have many archived emails that I stayed in the old world of Live Mail.

There are only a few folders that I would want to bring over from Live Mail to Outlook, the rest I can leave in Live Mail. The ones I leave, I can still access with Live Mail, if I ever need them. So, can either of you guys tell me how to move folders (preferably) or emails to Outlook? The most arduous way would be to send those emails to myself and once in Outlook, I can set up folders and deposit them in the new folders. Hopefully you have a better solution.
Anonymous

2026-06-24T03:09:13.6066667+00:00
Hi Reinhart Evelein,

I think that's a very reasonable approach. Since you've already confirmed that Outlook can send and receive mail successfully with your Shaw account, using Outlook as your primary mail client may be the least disruptive path forward.

Before suggesting the export steps, could you confirm Which version of Outlook are you using?

Classic Outlook for Windows (included with Microsoft 365 or Office)

New Outlook for Windows
Reinhart Evelein 0 Reputation points

2026-06-24T14:39:04.94+00:00

I believe I'm using New Outlook for Windows. The below came up in the "About", plus, there is a tab "Go to Classic Outlook" which implies I'm in New Outlook.

Microsoft Outlook Version: 1.2026.609.400

Client Version: 20260612016.19

WebView2 Version: 149.0.4022.80 (Stable)

Session ID: Removed PII
Reinhart Evelein 0 Reputation points

2026-06-24T14:56:57.81+00:00

Also, I'm trying to export my contacts list from Live Mail to Outlook and haven't figured it out yet. Please help. Thank youl
Anonymous

2026-06-27T03:15:39.79+00:00
Hi Reinhart Evelein,

Thank you for confirming. Based on the version information and the presence of the "Go to Classic Outlook" option, it does sound like you're using New Outlook for Windows.

Regarding your contacts, please follow this:

In Windows Live Mail, open Contacts.

Click Export and choose Comma Separated Values (.CSV).

Save the CSV file to a location you can easily find.

Go to your New Outlook

Go to People > Import contacts.

Select the CSV file and complete the import.

If any issue appears, try sign in to Outlook on the web at https://outlook.live.com and go to People tab > Import contacts. Once the contacts appear in Outlook on the web, they should sync automatically to New Outlook.

For your email folders:

In Windows Live Mail, locate the folder containing the messages you want to keep.

Export or copy those messages to a folder in File Explorer so that the individual .eml files are visible.

In New Outlook, go to "Settings" > "Data files" > "Import".

Under "Email Files (.eml)", select "Start import" and choose the folder containing the exported email files.

Since you only want to bring over a few important folders, importing selected folders as .eml files may be much easier than migrating your entire Windows Live Mail archive.
Reinhart Evelein 0 Reputation points

2026-07-01T22:16:11.2633333+00:00

I have just got an email from Rogers (the Shaw email provider) that they are "updating our outgoing mail server to improve its security". They must have gotten feedback from other's outgoing mail also not working. I will see if they fix my Live Mail, but then I have a delema. Do I continue with Outlook or go back to Live Mail.

I have brought my Contacts over to Outlook, and tested out the email export/import and have found subfolders need to be separately brought over, plus the email date is now the current date. I don't like that.

Anyway, stay tuned.
Anonymous

2026-07-02T03:49:49.8133333+00:00

Hi Reinhart Evelein,

Thank you for the update. If Rogers has recently updated their outgoing mail server settings or security requirements, that could certainly be relevant to the behavior you're seeing in Windows Live Mail.

For now, I'd suggest holding off on any large-scale migration until you see whether the Rogers changes have any impact on Windows Live Mail. If they do, you'll have a clearer choice between continuing with Live Mail or moving fully to Outlook.

Also, thank you for sharing your findings about the subfolder imports and message dates. That information may help other users considering a similar migration path.

Answer 2

Reinhart Evelein 0

I used Rogers webmail and sent a simple message. It did go and the receiver did receive it.

Ian-T 11,970 Reputation points Microsoft External Staff Moderator

2026-06-17T13:51:39.4933333+00:00

Great to hear that your emails are working fine now - Please correct me if I'm wrong. Thank you for the update

Hope you have a great day
Reinhart Evelein 0 Reputation points

2026-06-17T20:56:45.1333333+00:00

Ian, you misunderstood!!! My regular email app (Windows Live Mail) still doesn't send mail. It just sits in the Outbox and goes nowhere!! My frustration is even higher now!!
Anonymous

2026-06-18T03:34:16.9566667+00:00
Hi Reinhart Evelein,

Apologize on behalf of Ian-T's misunderstanding. The fact that the message sends successfully through Rogers Webmail but remains stuck in the Outbox in Windows Live Mail is actually a very helpful finding.

Since sending works from Webmail, this narrows the problem down to Windows Live Mail on this PC.

As a quick check, could you please confirm:

When you double-click a message that is stuck in the Outbox, then click Send/Receive, does the message remain in the Outbox or does it move to another folder (such as Drafts, Sent Items, or Deleted Items)?

Open Windows Live Mail and go to "File" > "Options" > "Email accounts", select your Shaw account, and click "Properties". Under the "Advanced" tab, what are the values shown for:

Outgoing mail (SMTP) port

Whether "This server requires a secure connection (SSL)" is checked

Approximately how old is this email account configuration? Has it been working unchanged for years before the June update?

Based on the fact that the issue started immediately after the update and affects only Windows Live Mail, it is possible that Windows Live Mail is no longer able to successfully negotiate the security settings required for outgoing mail. The answers above will help confirm whether that is the case before we make any changes.
Reinhart Evelein 0 Reputation points

2026-06-18T13:34:06.7366667+00:00
Answers to above:

The message remains in the outbox and goes nowhere else.

The "Options" category in Live Mail is under "Go". There is an "Advanced" tab but it does not have the question re the SSL secure server. However, under "Window" "Settings" "Accounts", "Email & accounts" my email appears there with a "Manage" box attached to it. It has a box to check off for "Require SSL for outgoing email" and the box is checked off.

My email Outbox has worked for years before this update. I seem to recall something years ago that was easily fixed, but that was a long time ago.
Anonymous

2026-06-21T00:30:34.1833333+00:00
Hi Reinhart Evelein,

Thank you for checking. This gives us a much clearer picture.

Based on your answers, I don't think we need to investigate the Rogers account itself any further. The problem appears to be specific to how Windows Live Mail is communicating with the outgoing mail server.

Before suggesting more changes, I'd like to narrow down one final point:

1, In Windows Live Mail, press Ctrl + Shift + O (or click "Show all folders" if available).

Do you see an "Errors" folder?

If yes, are there any recent entries around June 4-5 or when you attempt to send?

2, When you click "Send/Receive", does the status bar at the bottom show any message such as:

"Connecting..."

"Authorizing..."

"Sending..."

Or does it finish immediately with no message?

3, You mentioned checking Windows Settings > Email & accounts. To confirm, are you actually sending mail from Windows Live Mail 2012 (the older desktop program), and not from the built-in Windows Mail app?

I'm asking because Windows Live Mail and the Windows Mail app store account settings separately. If we're looking in the wrong place, the SSL setting you found may not be the one Windows Live Mail is actually using.

At this point, it seems the recent Windows update affected how Windows Live Mail negotiates the secure SMTP connection, but I'd like to confirm whether Windows Live Mail is reporting any hidden send errors before suggesting account reconfiguration.
Reinhart Evelein 0 Reputation points

2026-06-22T14:36:44.9433333+00:00

Thanks Sin-D. I can confirm that I am able to send and receive mail from the same, [Removed PII]@shaw.ca, account.

Answer 3

Anonymous

Please note that our forum is a public platform, and we will modify your question to hide your personal information in the description. Kindly ensure that you hide any personal or organizational information the next time you post an error or other details to protect personal data.

Hi Reinhart Evelein,

I understand how frustrating it can be when you suddenly can’t send emails, especially after a Windows update.

To better isolate the issue, could you confirm:

Which app are you using to send emails?
What exactly happens when you try to send? Do you get any error message (if yes, what does it say)?
Did anything else stop working after the update?
Check Windows services impact (quick yes/no):
- Press Windows + R, type “services.msc”
- Look for “Sync Host_…” services, are they running or stopped?
Have you already tried the steps suggested by Q&A Assist?

Once I have these details, I can pinpoint the cause and give you targeted steps.

Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.

Anonymous

2026-06-11T03:59:58.23+00:00

Hi Reinhart Evelein,

Have you had the chance to check my answer yet?

Please do keep me updated.
Reinhart Evelein 0 Reputation points

2026-06-11T12:46:32.2633333+00:00
I'm using Live Mail and Windows 10. I know it's old but I have a ton of folders with stored emails I don't want to get rid of.

I got an update June 4, 5 ?, and I got an error message which I cannot replicate now, because yesterday June 10, I got another update. When I try to send a simple email (1 address, not attachment, just a title), it tries to send, but I now get nothing. No error message and the email still sits in the Outbox.

As far as I can tell, everthing works. after the June 4,5? update, Microsoft Edge took a day to work, but then worked fine.

No. I got nothing after typing in "services msc".

I did try most of the steps, but didn't try step 6. I'm not confident in typing code. Step 7. I found I had 2 identical email accounts. The first had the right SMPT info for outgoing mail. The "Require SSL for outgoing mail" was not checked off, so I checked it off. The second, called "Shaw 2" was a mystery to me. It didn't have anything that looked right, so I deleted it. Nothing changed. Still no simple mail going out.
Anonymous

2026-06-13T04:19:18.6666667+00:00
Hi Reinhart Evelein,

Thanks for the detailed follow‑up.

Additionally, please try to test sending via webmail

Go to Shaw webmail (via browser like Edge)

Send a simple email

If it sends, confirms issue is Windows Live Mail only

If it fails, could be account/provider related

Also, since you already adjusted SMTP once, try this specific check:

Open your account settings

Go to Servers tab

Confirm:

“My server requires authentication” = checked

Go to Advanced tab

Outgoing (SMTP) port = 587

“This server requires a secure connection (SSL)” = checked

Use port 587 (not 25 or 465), as many providers now block older ports.
Ian-T 11,970 Reputation points Microsoft External Staff Moderator

2026-06-17T10:33:15.8766667+00:00

Hi

I’m following up to check on the status of this issue.

Have you had an opportunity to review the answer shared earlier?

Any update you can provide would be greatly appreciated.