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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Answer 1

Reinhart Evelein 0

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

Ian-T 7,770 Reputation points Microsoft External Staff Moderator

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

Great to hear that your emails are working fine now. 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!!
Sin-D 10,315 Reputation points Microsoft External Staff Moderator

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

I understand your frustration. 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.

Answer 2

Sin-D 10,315 Microsoft External Staff Moderator

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.

Sin-D 10,315 Reputation points Microsoft External Staff Moderator

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.
Sin-D 10,315 Reputation points Microsoft External Staff Moderator

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 7,770 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.

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Emails outgoing not working

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