Using Classic Outlook on Windows for personal email, calendar, and contact management
Please reply with these details so the issue can be narrowed down:
- The exact error message Outlook shows during the test.
- Whether webmail works for the same mailbox.
- Whether the mailbox is hosted by Microsoft 365, cPanel, GoDaddy, another web host, or an ISP.
- The provider-confirmed encryption type for POP and SMTP.
- Whether the old file is a .pst file and whether it opens successfully by using File > Open & Export > Open Outlook Data File.
Try these steps:
1) Confirm the mail provider’s current POP and SMTP requirements first
Before changing Outlook again, please confirm these exact settings with your email administrator or hosting provider:
- Whether POP is still enabled for the mailbox.
- Whether POP port 110 is allowed, or whether the provider requires encrypted POP on a different port.
- The required encryption type for incoming POP.
- Whether SMTP port 587 requires STARTTLS.
- Whether SMTP authentication is required.
- Whether the username must be the full email address.
- Whether the account requires an app password or special mail password instead of the normal webmail password.
If the provider is not listed, you should contact the ISP or email administrator for the correct incoming/outgoing server names, ports, and SSL settings.
2) Check the outgoing server authentication setting
In Classic Outlook:
- Go to File > Account Settings > Account Settings.
- Select the POP account, then choose Change or Repair, depending on what appears.
- Open More Settings.
- Go to the Outgoing Server tab.
- Enable My outgoing server (SMTP) requires authentication.
- Select Use same settings as my incoming mail server.
- Go to the Advanced tab and confirm the POP and SMTP ports/encryption match the provider’s current settings.
- Save, restart Outlook, then test again.
This setting is commonly required for SMTP port 587
3) Do not attach the old Outlook 2016 data file during the first account test
Since you are trying to connect while also pointing the account to an existing Outlook 2016 data file, isolate the issue first:
- Create the account in Outlook without using the old data file during the first test.
- Let Outlook create a new data file.
- Confirm whether the account can connect, receive, and send.
- After the account works, open the old data file separately by going to File > Open & Export > Open Outlook Data File.
If the account works with a new data file but fails when using the old one, the issue may be with the old PST file rather than the POP/SMTP connection.
4) Repair the old Outlook data file if you need to keep using it
If the old PST file came from the Windows 10 / Outlook 2016 system, repair it before using it as the default delivery file:
- Close Outlook.
- Run SCANPST.EXE, the Inbox Repair Tool.
- Browse to the old .pst file.
- Start the scan.
- If errors are found, choose Repair.
- Open Outlook again and test.
5) Create or repair an Outlook profile if the same settings keep failing
If the provider confirms the settings are correct but Outlook still will not connect, try repairing the Outlook profile first:
- In Outlook, go to File.
- Select Account Settings > Account Settings.
- On the Email tab, select the account.
- Choose Repair.
- Follow the prompts, then restart Outlook.
If repairing the profile does not help, create a fresh Outlook profile:
- Close Outlook.
- Open Control Panel.
- Search for Mail.
- Select Show Profiles.
- Create a new profile.
- Add the POP account manually using the provider-confirmed settings.
- Set Outlook to prompt for a profile, then open the new profile and test.
This helps avoid corruption or bad settings carried over from the older Outlook setup.
6) If it still fails, test outside Outlook
To separate an Outlook problem from a server/provider problem:
- Confirm you can sign in to the mailbox through webmail.
- Ask the provider whether the mailbox accepts POP connections from outside their network.
- Ask whether the provider blocks plain POP on port 110 or requires encrypted POP.
- Ask whether SMTP port 587 is enabled for authenticated sending.
- If possible, test the same POP/SMTP settings in another mail app.
If webmail works but POP/SMTP fails in every mail app, the email host must correct the server-side POP/SMTP access or provide the correct current settings.
Please tell me how it goes. If the problem persists, please don’t hesitate to reply to this thread and I will be happy to help. Have a lovely day!
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