Sending email using Outlook

Question

I am using Outlook for Mac version 16.109.3 with a Shaw/Rogers IMAP account. Outlook receives email normally but cannot send. Messages remain in the Outbox and Outlook reports 'Connection to the server failed or was dropped.' Shaw Webmail sends and receives correctly, and I have already verified smtp.shaw.ca, ports 587 and 465, authentication settings, and password credentials.

Answer 1

If you're trying to send emails using Outlook, the exact setup depends on whether you're using Outlook as an email client or sending emails programmatically from an application.

For the Outlook desktop client, first verify that your account is configured correctly and that SMTP authentication is enabled. Also check that you're using the correct outgoing server, port (typically 587 with STARTTLS or 465 with SSL/TLS, depending on your email provider), and valid account credentials. Incorrect SMTP settings are one of the most common reasons emails fail to send.

If you're sending emails from your own application, it's generally better to use your mail provider's SMTP server or an email API rather than automating the Outlook application itself. A reliable SMTP service provider such as iDealSMTP can be a good option for transactional or bulk emails, while providers like Mailgun and Brevo are also commonly used depending on your requirements.

If you can share how you're sending the email (Outlook desktop, Outlook.com, Microsoft Graph API, SMTP, C#, Python, etc.) and any error message you're seeing, it will be easier to suggest the appropriate solution.

Answer 2

@Paul Griffiths said

Apple Mail successfully sends through Shaw SMTP on the same Mac using the same credentials. Outlook 16.109.3 receives mail but cannot send.

Ongoing thread on this problem on Reddit Outlook.
[External Non-Microsoft Site] https://www.reddit.com/r/shaw/comments/1ru4qsa/shaw_email_outbound_email_in_outlook_broken/

Seems to just come-and-go for no apparent reason. Sorry but I don't see any real fix or workarounds.

Accessing the account from native Mail app, iPhone mail app, direct on webmail.shaw.ca all work. This seems specific to Outlook on Mac.

Mine started working again briefly then died again. Haven’t heard anyone in this thread say it was resolved (other than me thinking it was for a brief period of time).

Answer 3

Hi Paul Griffiths,

I understand that Outlook for Mac can receive messages from your Shaw/Rogers IMAP account, but sent messages remain in the Outbox with “Connection to the server failed or was dropped.”

Please note that this is a user-to-user forum, so contributors can share troubleshooting suggestions, but account-side SMTP restrictions need to be confirmed by Shaw/Rogers.

I would just like to add one Shaw/Rogers-specific point. Since you have already checked the SMTP server, ports, authentication settings, and password, please also confirm that mail client access is enabled in Shaw Webmail:

1. Sign in to Shaw Webmail from a browser.
2. Make sure Webmail is using Classic mode.
3. Open Preferences.
4. Go to Access from Other Mail Client.
5. Make sure mail client access is enabled.

Rogers states that IMAP or POP access requires Webmail to be in Classic mode and mail client access to be enabled. Reference: Shaw Email: Which email setup method is right for me and how to enable it?(Disclaimer: This is a non-Microsoft website. The page appears to be providing accurate, safe information. Watch out for ads on the site that may advertise products frequently classified as a PUP (Potentially Unwanted Products). Thoroughly research any product advertised on the site before you decide to download and install it. Microsoft provides no assurances and/or warranties, implied or otherwise, and is not responsible for the information you receive from the third-party linked sites or any support related to technology.)

If this is already enabled and the issue continues, it would be best to ask Shaw/Rogers to confirm whether SMTP submission is allowed for your mailbox from your current network, since Webmail can send but Outlook cannot connect to the SMTP service successfully.

Microsoft’s related Outlook for Mac guidance is also available here: I can't send or receive messages with Outlook for Mac

I hope this provides the next steps to narrow down whether the issue is related to Outlook’s local connection path or Shaw/Rogers mailbox-side SMTP access.

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Answer 4

Based on the symptoms and what has already been checked, focus on Outlook for Mac’s connection state, SMTP authentication, and any network/firewall issues between Outlook and Shaw/Rogers.

Try the following in order:

1. Confirm Outlook and Mac connectivity

• In Outlook for Mac, on the Outlook menu, make sure Work Offline is not checked so Outlook is online.
• In Safari or another browser, verify that general Internet access works and that Shaw Webmail can send mail from the same account. This confirms the account itself is healthy.

2. Re‑check SMTP authentication in Outlook for Mac Even if authentication was already reviewed, explicitly re‑set it, as mis‑negotiated SMTP auth is a common cause of send failures with IMAP accounts.

• In Outlook for Mac, select Tools > Accounts.
• Select the Shaw/Rogers IMAP account in the left pane.
• Under Outgoing server, click More Options.
• Ensure an authentication method is selected (for most ISPs this is typically the same username/password as the incoming server) and re‑enter the credentials.
• Save and test sending again.

If SMTP authentication is off or misconfigured, Outlook may connect but the server will drop the connection when sending.

3. Verify full IMAP/SMTP settings in the account

• In Tools > Accounts, select the account and confirm:
  • Email address, User name, and Password are correct.
  • Incoming server and Outgoing server values match the details from Shaw/Rogers.
  • If Shaw/Rogers requires SSL or specific ports, select Override default port and Use SSL to connect (recommended) on both incoming and outgoing servers, and set the ports exactly as provided by Shaw/Rogers.
• If unsure about SSL/port requirements, check Shaw/Rogers’ documentation and adjust accordingly.

4. Check for firewall or ISP blocking of SMTP The specific error “connection to the server failed or was dropped” when sending, while receiving works, often indicates that outbound SMTP is being blocked or interfered with.

• If using a local firewall or security software on the Mac, temporarily disable it and test sending.
• If on a managed or corporate network, contact the network admin or ISP and ask whether connections to the Shaw SMTP server/ports (587/465) are being blocked.
• If Shaw/Rogers provides an alternative SMTP server or port, configure it:
  • Tools > Accounts > select account.
  • In Outgoing server, enter the alternative SMTP server name.
  • Adjust port/SSL settings as required and test.

5. Confirm no proxy requirement If the network requires a proxy to reach external mail servers and it is not configured, SMTP connections can fail.

• In macOS System Settings (or System Preferences on older versions), check the network’s proxy settings.
• If a mail proxy is required, obtain the correct settings from the network administrator and configure them there.

6. Verify mail server availability

• Since Shaw Webmail works, the account is active, but the specific SMTP endpoint used by Outlook could still be experiencing issues.
• If the problem persists after the above steps, contact Shaw/Rogers support with the exact error and confirm:
  • The correct SMTP hostname, port, and encryption settings for third‑party clients.
  • That the account is allowed to send via SMTP from the current network/location.

If, after all of the above, Outlook still cannot send while Webmail works, the next step would be to remove and re‑add the IMAP account in Outlook for Mac using the provider’s current settings, then test again.

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References:

• I can't send or receive messages with Outlook for Mac
• Basic IMAP account settings for Outlook for Mac
• Basic POP account settings in Outlook for Mac
• Outlook for Mac Help