Windows 10 Problem with Outlook 2021 continued

[John Clark]

I had to delete my original account (pop) then started a new one. My original data file ( .pst ) was stored on another drive so when I reestablished my account in Outlook it created an .ost file under USER\APPDATA....OUTLOOK\username.ost. I realized this morning that outlook is using the .pst data file for all new email in lieu of the default ost data file where all of my previous data is relocated.
My other devices, cell phone and laptop (both imap), have some how loaded old deleted files from the server into the Inbox with new emails. Do I transfer (copy) all data over to the pst data file? If I remember from 3 days ago, emails came in on the ost file but now the pst file. What a nightmare created from outlook's hiccup.

 

[ChatGPT]

It looks like you're experiencing some frustrating issues with Outlook's POP3 account setup. Given the errors you're encountering, let's troubleshoot the situation step-by-step, focusing on the settings and the common causes for these errors.

Errors Breakdown:​

1. Incoming Mail Server Error:
   • Error Message: "Your email server rejected your login. Verify your user name and password for this account."
   • This implies that Outlook is not able to authenticate with the credentials you are providing, which can happen for several reasons:
     • Ensure that you are entering the full email address as the username. This is critical in many configurations.
     • Double-check the password. Even if it works on the web, there might be hidden characters or caps lock issues when typed into Outlook.
2. Sending Email Error:
   • Error Message: "530 5.7.57 Client not authenticated to send mail."
   • This suggests that while the POP3 account might be set up, the SMTP server isn't allowing you to send emails. The common causes include:
     • The SMTP settings might not align correctly. Ensure you are using the email address and password, and that the server settings are accurate.
     • Authentication issues—ensure that "My outgoing server (SMTP) requires authentication" is checked in the settings.

Recommended Settings​

Here’s a recap of the settings, ensuring that everything aligns properly:

• Incoming Mail (POP3) Settings:
  • Server: outlook.office365.com
  • Port: 995
  • Encryption Method: SSL/TLS
• Outgoing Mail (SMTP) Settings:
  • Server: smtp.office365.com (note the server name should be smtp.office365.com, not smtp-mail.outlook.com)
  • Port: 587
  • Encryption Method: STARTTLS
  • Ensure that "Use same settings as my incoming mail server" is checked for authentication.

Troubleshooting Steps​

1. Re-enter Username and Password:
   • Go to File > Account Settings > Account Settings, select your account, and click on Change. Re-enter your password carefully.
2. Modify Server Settings:
   • Ensure that the SMTP server is set to smtp.office365.com instead of smtp-mail.outlook.com.
3. Test with an App Password:
   • If you have Two-Factor Authentication (2FA) enabled on your Microsoft account, you may need to create an app-specific password through your Microsoft account security settings and use that password in Outlook instead of your standard password.
   • Visit Sign in to your Microsoft account and look for app passwords to generate one.
4. Use Microsoft Support and Recovery Assistant:
   • Microsoft offers a tool to assist with account setup that might help automate the troubleshooting process.
   • You can download it from this link: Microsoft Support and Recovery Assistant.
5. Log into the Webmail First:
   • Ensure you can log into your webmail interface using the same email and password one more time before retrying the POP setup, as this confirms account access integrity.
6. Firewall/Antivirus:
   • Temporarily disable your firewall or antivirus software and try the setup again, as they can sometimes interfere with authentication.

Conclusion​

By carefully verifying these details and following through these troubleshooting steps, you should be able to resolve the issues you're experiencing with setting up your POP3 email account in Outlook. If you continue to have problems, sharing specific error messages received during each step can provide further insights into what might be happening. Let me know how it goes!

 

[John Clark]

doesn't work. RATHER TALK WITH MODERATOR

 

[ChatGPT]

It seems like you're at a frustrating point in your attempts to set up the POP3 account in Outlook, and I understand your desire to speak with a staff member for more personalized assistance. While I can't directly transfer you to a moderator, I can provide a summary of what you've been through and some next steps you might consider:

Summary of Your Situation:​

1. Email Setup Attempts: You’ve been trying to set up a POP3 email account in Outlook using Office Professional 2021, but have encountered various errors.
2. Server Settings: You’ve configured the settings with:
   • POP server: outlook.office365.com
   • SMTP server: smtp.office365.com
   • Ports and encryption: Correctly specified as per the guidelines.
3. Persistent Errors:
   • Errors related to logging into the incoming mail server and issues with sending email due to authentication problems.

Recommended Next Steps:​

1. Contact Microsoft Support: Since you've experienced repeated issues, it might be beneficial to reach out to Microsoft Support. They have tools and resources to provide direct assistance.
   • You can contact them through this link: Microsoft Support.
2. Use the Microsoft Support and Recovery Assistant:
   • This tool can help automate troubleshooting for Outlook-related issues and may resolve current problems you're facing during setup.
   • Download it from: Microsoft Support and Recovery Assistant.
3. Revisit Account Configuration:
   • If you're open to trying again before seeking direct support, ensure that all credentials entered are as required, double-checking for typos, ensuring the email is entered correctly as a username, and confirming the password.
4. Review Firewall and Antivirus Settings:
   • Temporarily disable any security software agreements you have to check if they’re affecting your connection.

Conclusion​

If you're not satisfied with the options here or the previous advice given, definitely reaching out to a support representative can provide the help and reassurance you need. Please let me know if you need assistance with any specific parts of this process, or if you'd like to attempt more troubleshooting together. Your patience is appreciated, and I'm here to support you!

 

[ChatGPT]

It seems like you're at a frustrating point in your attempts to set up the POP3 account in Outlook, and I understand your desire to speak with a staff member for more personalized assistance. While I can't directly transfer you to a moderator, I can provide a summary of what you've been through and some next steps you might consider:

Summary of Your Situation:​

1. Email Setup Attempts: You’ve been trying to set up a POP3 email account in Outlook using Office Professional 2021, but have encountered various errors.
2. Server Settings: You’ve configured the settings with:
   • POP server: outlook.office365.com
   • SMTP server: smtp.office365.com
   • Ports and encryption: Correctly specified as per the guidelines.
3. Persistent Errors:
   • Errors related to logging into the incoming mail server and issues with sending email due to authentication problems.

Recommended Next Steps:​

1. Contact Microsoft Support: Since you've experienced repeated issues, it might be beneficial to reach out to Microsoft Support. They have tools and resources to provide direct assistance.
   • You can contact them through this link: Microsoft Support.
2. Use the Microsoft Support and Recovery Assistant:
   • This tool can help automate troubleshooting for Outlook-related issues and may resolve current problems you're facing during setup.
   • Download it from: Microsoft Support and Recovery Assistant.
3. Revisit Account Configuration:
   • If you're open to trying again before seeking direct support, ensure that all credentials entered are as required, double-checking for typos, ensuring the email is entered correctly as a username, and confirming the password.
4. Review Firewall and Antivirus Settings:
   • Temporarily disable any security software agreements you have to check if they’re affecting your connection.

Conclusion​

If you're not satisfied with the options here or the previous advice given, definitely reaching out to a support representative can provide the help and reassurance you need. Please let me know if you need assistance with any specific parts of this process, or if you'd like to attempt more troubleshooting together. Your patience is appreciated, and I'm here to support you!

 

[Neemobeer]

I didn't bother to read the massive thread, but is this a business email or personal?

If you are using pop3 then it should use a PST file, but if your connecting via IMAP or MAPI then Outlook will always use an OST file. You should be able to add the PST file though and move that data into the OST

 

[ChatGPT]

For POP3 email accounts configured with Office 365 (Outlook.com), the outgoing email server (SMTP) settings differ slightly from older configurations like outlook.exchange365.com. Here’s a summary of the correct server settings for outgoing email:

Outgoing Mail Server (SMTP) Settings​

• Server name: smtp.office365.com
• Port: 587
• Encryption type: STARTTLS (or TLS, depending on the client’s options)
• Authentication: Ensure "My outgoing server (SMTP) requires authentication" is checked. Use the same email address and password as your incoming mail credentials.

Important Notes​

1. Deprecation of outlook.exchange365.com:
   • The URL outlook.exchange365.com is outdated and not officially supported for modern Office 365-based configurations. Transition to the more reliable setting, smtp.office365.com, to ensure compatibility.
2. Two-Factor Authentication (2FA):
   • If your account uses Microsoft's Two-Factor Authentication, you'll need to generate an app password for Outlook. This is configured in your Microsoft account settings under security.
3. Authentication and Username:
   • Always use your full email address as the username (e.g., [email protected]).
   • For the password, use either your regular account password or app password (if 2FA is enabled).
4. Diagnose with Microsoft Support Tools:
   • If errors persist, download and use Microsoft's Support and Recovery Assistant tool (link here) to identify any configuration mistakes or connection issues.

Conclusion​

Switch your SMTP server to smtp.office365.com, verify settings as listed above, and ensure strong authentication. If you're still running into issues, feel free to share specific errors, and I’ll help you further troubleshoot. Good luck!