I'm not able to send outgoing emails.

Question

I'm not able to send outgoing emails.

Margaret Burkesmith 15

I'm not able to send outgoing emails as of Monday 3/23/2026. I had the help of an e-mail support person on Microsoft Chat - who worked on the issue for over 45 minutes. Here is the case no.#[Moderator Note: Personal Info Removed]. He suggested that I continue working with you, as the problem has not been resolved as of 3/24/2026 at 9:09pm.

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Lynda Wallace-Hulecki 0 Reputation points

2026-03-29T19:42:33.2933333+00:00

Microsoft Outlook for MAC is not syncing with [Moderator Note: Personal Info Removed].ca outgoing email server. Shaw support indicates the account settings are all correct and it's an Outlook issue. Please advise how to resolve

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Lynda Wallace-Hulecki 0 Reputation points

2026-03-29T19:42:33.2933333+00:00

Microsoft Outlook for MAC is not syncing with [Moderator Note: Personal Info Removed].ca outgoing email server. Shaw support indicates the account settings are all correct and it's an Outlook issue. Please advise how to resolve

Answer 1

Chloe-V 7,260 Microsoft External Staff Moderator

Hi Margaret Burkesmith,

Welcome to Microsoft Q&A forum.

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.

To quickly narrow down why you’re unable to send emails, could you please confirm the two items below:

Which app are you sending from: Outlook on the web, Classic Outlook on your computer, the new Outlook, or the mobile app?
What happens when you click Send: does the message get stuck in the Outbox, or do you receive a notification/bounce‑back? If so, please paste the exact wording via private message.

Once I have these details, I’ll be able to identify the most appropriate next 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.

Chloe-V 7,260 Reputation points Microsoft External Staff Moderator

2026-03-29T07:45:03.09+00:00

Hi Margaret Burkesmith,

Is there any update from you?

If yes, please feel free to let us know.
Margaret Burkesmith 15 Reputation points

2026-03-29T19:20:32.3633333+00:00

Hello Cloe,

Thank you for your outreach.

I use Classic Outlook on my Computer. I get a bounce-back message - no matter who I send it to.

Bounce-back reads: Your message wasn't delivered because the recipient's email provider rejected it. Message blocked because it contains content identified as spam. AS(4810)>

However, I have since switched to my Microsoft Edge Browser and it seems to be working better. And, I no longer send outgoing emails via my other devices - which may help as well?

Thank you for your assistance, Margaret'
Lynda Wallace-Hulecki 0 Reputation points

2026-03-29T19:44:06.7633333+00:00

I am using the Classic app and when sending emails, they get stuck in the Outbox.
Chloe-V 7,260 Reputation points Microsoft External Staff Moderator

2026-03-30T02:12:58.3033333+00:00
Hi Margaret Burkesmith and Lynda Wallace-Hulecki, thank you both for sharing the additional details.

Based on the behavior described (bounce-back errors, messages flagged as spam, or emails getting stuck in the Outbox), this may be related to PDF attachments and/or Rich Text/HTML formatting. Many email providers have recently tightened spam filtering, and PDFs are commonly scrutinized due to phishing activity.

To help narrow this down, please try the following:

Send the same email without the PDF attachment and check whether it sends successfully.

If you need to include the file, try sharing it via a OneDrive link instead of attaching it.

Additionally, test changing the email format to Plain Text before sending.

As a comparison, please also try sending from Outlook on the web to see whether the behavior differs from Classic Outlook.

Please let us know which option works (if any). This will help determine whether the issue is related to the attachment, message format, or the desktop app itself.
Chloe-V 7,260 Reputation points Microsoft External Staff Moderator

2026-03-31T06:14:33.8+00:00

Hi

Is there any update from you?

If yes, please feel free to let us know.
Debbie Delamont 0 Reputation points

2026-03-31T09:40:56.03+00:00

Please can you tell me how I can get in touch with someone to help. Thanks
Lynda Wallace-Hulecki 0 Reputation points

2026-03-31T17:38:11.3333333+00:00

There were no attachments to my sent emails. I tried resetting the account by deleting it from Outlook and adding it back in. That did not address the issue. the emails continue to get stuck in the outbox.

I took my MAC into a third party Apple technical support group who tried multiple options to resolve the matter and finally performed a "work-around" through the use of MAC mail. This is not ideal.
Chloe-V 7,260 Reputation points Microsoft External Staff Moderator

2026-03-31T23:34:46+00:00
Hi

I’m sorry to hear about the ongoing inconvenience you’re experiencing—especially after already trying multiple troubleshooting steps and even a third‑party workaround. I understand how frustrating this can be when email functionality is impacted.

Since the issue persists and requires account‑level investigation, the next step is to contact Microsoft Support so they can review this in a private support session.

You can reach Microsoft Support by following the steps below:

Go to Contact Us: https://support.microsoft.com/en-us/contactus

Click Show expanded list of products

Select Outlook > Get Home support

Type Outlook live chat in the search box, then select Get Help > Contact Support

If you can’t sign in to the affected account, sign in with a different Microsoft account to access support options

Under Products & Services, select Other Products > Outlook, then choose Chat with a support agent via web browser

Thank you for your time and understanding.
Margaret Burkesmith 15 Reputation points

2026-04-01T01:34:40.19+00:00

thank you Chloe-V,

I will also try to reach Microsoft Support. Which is a step I initially tried, then they suggested I come to this support system. Yet, I will try again.

My update is that my outgoing emails are working if it's simple plain text like you suggested. If there's any link in it, including from OneDrive, it gets rejected.

[Moderator Note: Personal Info Removed]
Chloe-V 7,260 Reputation points Microsoft External Staff Moderator

2026-04-02T06:18:33.9233333+00:00

Hi Margaret Burkesmith,

Thank you for the update.

Please note that this is a user‑to‑user support forum. Moderators and contributors, including external Microsoft staff, are not able to directly intervene in Microsoft product features or access server‑side systems. Our role is limited to providing technical guidance on reported issues, requests, or ideas.

If you receive any additional information or instructions from Microsoft Support, you’re welcome to share an update here.

Thank you for your understanding.

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I'm not able to send outgoing emails.

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