Error code -17895

Question

I had to contact a software company via email. Their contact was <Mod remove PII>. I created an email with that address. Outlook for Mac could not send the email because of Error Code -17895 Authentication failed because Outlook doesn't support any of the available authentication methods. Outlook keeps trying to this email over and over again. The email DOES NOT show in my Drafts folder. I have no idea where it is so I could delete it. I don't have any trouble sending or receiving other emails. I WANT TO DELETE THIS EMAIL. I DON'T NEED TO SEND IT. Please, anybody, HELP. I’m running Microsoft Outlook for Mac, Version 16.101.3 (25100321.

Answer 1

Dear Charles Curry, Thank you for reaching out to the Microsoft Q&A Community. I understand that you are experiencing an issue where Outlook for Mac cannot send an email due to Error Code -17895 and you want to delete the stuck email. I am happy to assist you with that.
Please try the following steps:
Step 1: Switch to Legacy Outlook (if using New Outlook)

• Open Outlook for Mac.
• Go to Help > Revert to Legacy Outlook.
• After reverting, check the Outbox folder and delete the stuck email.

Step 2: Work Offline and Delete the Email

• In Outlook, select Outlook > Work Offline.
• Navigate to the Outbox folder.
• Delete the stuck message.
• Return to Outlook > Work Online.

Step 3: Search for the Email

• Use the Search bar in Outlook.
• Enter part of the recipient’s email address (e.g., aimor.app).
• If the email appears, delete it.

Step 4: Check Sync Errors

• Go to Tools > Sync Errors.
• If the email is listed there, delete it.

Step 5: Rebuild Outlook Database (if necessary)

• Close Outlook.
• Hold the Option key and click the Outlook icon.
• Select Rebuild.
• After the rebuild, the stuck email should be removed.

For more details, please refer to these resources:

Outlook email stuck – Microsoft Support

Fixes or workarounds for recent issues in Outlook for Mac

Fix authentication issue in Outlook for Mac

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Answer 2

Dear Charles Curry, 

Thank you for updating us. Since the previous steps didn’t resolve the issue and now you cannot send any emails, please try these additional steps: 

Step 1: Verify Account Settings 

1. In Outlook, go to Tools > Accounts. 
2. Select your email account and confirm: 
   1. Incoming/Outgoing server settings match your provider’s recommended configuration. 
      • Authentication is set to Username and Password (not NTLM or Kerberos). 
      • If unsure, check your email provider’s official settings page. 

Step 2: Remove and Re-add the Account 

1. In Tools > Accounts, select the problematic account and click – to remove it. 
2. Restart Outlook. 
3. Add the account again using the correct credentials and server settings. 

Step 3: Clear Outbox and Sync Cache 

1. Close Outlook. 
2. Navigate to: ~/Library/Group Containers/UBF8T346G9.Office/Outlook/Outlook 15 Profiles/Main Profile/Data/Messages/Outbox 
3. Delete any files inside the Outbox folder. 
4. Restart Outlook. 

Step 4: Rebuild Database (Correct Method) 

1. Close Outlook. 
2. Hold Option and click the Outlook icon. 
3. Select Outlook Profile Manager > Choose your profile > Click Rebuild. 

Step 5: Test in Safe Mode 

Run Outlook in Safe Mode to rule out add-in conflicts: 

a. Open Terminal and type: open -a "Microsoft Outlook" --args -safe 

b. If these steps do not resolve the issue, the next best option is to completely reinstall Outlook for Mac and ensure macOS is up to date. 

Step 6 : If all steps fail please kindly contact Microsoft Support   

Here comes the steps:  

1. Visit this website:  Contact - Microsoft Support  
2. Type your problems in the search box there. ( For example, Contact support.)  
3. Now click on Get Help and select Contact Support below.  
4. Go to the Products & Services tab and choose the Outlook category  
5. On the Category tab, choose based on your actual problem.
6. Go to Confirm.  
7. Choose to chat with a support representative or request a call back.  

Note: The support contact team only works at certain times, so if the last window shows that it's unavailable, try opening it again the next day. If you prefer phone support, you can leave a phone number. This way, they can call you and help you.  

I hope these steps help resolve your problem.    

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

Warm Regards 

Answer 3

Dear Charles Curry , 

Thank you for your patience, and I’m very sorry for the delay and inconvenience. Since sending fails on all your accounts, the most likely cause is SMTP authentication settings or modern authentication requirements. Please follow these steps:  

Step 1: Update SMTP Settings for Each Account 

1. In Outlook, go to Tools > Accounts.  
2. Select your account and click More Options under Outgoing Server.  
3. Set Authentication to Username and Password (not NTLM or Kerberos).  
4. Use these SMTP settings: 
   • Port: 587
   • Encryption: STARTTLS/TLS
   • Server names:
   • Outlook.com → smtp-mail.outlook.com
   • iCloud → smtp.mail.me.com (requires app-specific password)
   • Rainierconnect → use their published SMTP server name.
   • Enter your full email address and password.

Step 2: Generate App-Specific Password for iCloud 

1. Go to Apple Account.  
2. Sign in, then go to Security > App-Specific Passwords and generate one.  
3. Use this password in Outlook for iCloud SMTP.  

Step 3: Clear Stuck Outbox Items 

1. Close Outlook.  
2. Navigate to: ~/Library/Group Containers/UBF8T346G9.Office/Outlook/Outlook 15 Profiles/Main Profile/Data/Messages/Outbox 
3. Delete any files inside the Outbox folder.  
4. Restart Outlook.  

Step 4: Back Up POP Data Before Removing Accounts 

Because POP stores mail locally, back up first:  

1. Switch to Legacy Outlook (Help > Revert to Legacy).  
2. Go to Tools > Export.  
3. Choose Archive File (.olm) and include On My Computer items, Contacts, and Calendar.  
4. Save the file in a safe location.  

Step 5: Remove and Re-Add Accounts 

After backup:  

1. In Tools > Accounts, remove the problematic accounts.  
2. Restart Outlook.  
3. Add accounts again using the correct SMTP settings from Step 1.  

If these steps do not resolve the issue, please let me know . Thank you for your understanding and cooperation.  

Warm regards 

Answer 4

I need further explanations in Step1.4 (SMTP settings). Some fields are greyed out, the drop down lists, such as Encryption, do not list your suggested entries. I need to send you 14 screenshots. This chat software only lets me add 1 image per comment. Seems ridiculous to send 14 messages. I compressed them into 2 .zip files but your software does not recognize .zip files as valid files. How can I send them to you?