Dealing with Email Issues
If you have issues connecting with the Internet generally, you'll be unable to send or receive email. See Internet Connection Issues for troubleshooting tips.
See Computer Basics & Terminology for help with technical terms.
Importing/Exporting Mail, Contacts & Settings
When changing email programs, you'll want to import the mail, contacts and settings from the old program to the new one.
Many programs will import this information from the most common current programs and even a few of the older ones.
- Thunderbird can natively import/export address books, mail and settings in a number of formats.
- The Bat! imports and exports email messages in .MSG, .EML and UNIX mailbox formats and now supports Exchange Web Services (EWS) protocol. See Moving to The Bat! for help moving from Pocomail.
- Outlook see Outlook Resources for help in importing/exporting with Outlook.
Third-Party Import/Export Programs
These programs match the format of the data from program you're exporting from and convert it to the one you're importing this information into.
- Aid4Mail MBOX Converter (free edition) converts mbox-type mailboxes to EML files.
- Aid4Mail (from US$29.95) is an easy-to-use migration tool that can also archive mail.
Email Backup Software
You can use email backup software to both secure your important emails from loss as well as to restore it to another installation.
- Best free email backup software for Windows 10 from The Windows Club.
- How to backup Gmail emails using UpSafe GMail Backup freeware.
- MailStore Home is a free email archiving software for Windows PC.
If you decide to move to Outlook, be aware that I neither use nor recommend Outlook and therefore cannot provide the level of support I can with my recommended email programs. You'll need to find alternative support.
You need to be aware of the winmail.dat issue that affects users of many non-Microsoft email program users because it is invisible to you but can affect many of those you send emails to unless you're restricted to an office environment entirely composed of Outlook users.
Issues with Unsupported Versions
Don't use unsupported versions of Outlook. Like any program, the end of support means that the program no longer receives security fixes. There can also be compatibility issues with Microsoft servers.
Starting on November 1, 2021, only Office 2013 Service Pack 1, with up-to-date patches, and later Office releases will connect to Microsoft-hosted mailboxes.
Earlier versions of Office/Outlook, including Outlook 2007, Outlook 2010, and Office 2013 (before SP1) won't be able to connect. Office 2007 and Office 2010 are already out of support. Office 2013 extended support ends in April 2023.
— Ask Woody Newsletter
Outlook Support Resources
I've provided the following external resources to help you learn more about using Outlook and dealing with its issues.
Backing Up Outlook
- Manage, download, back up, or restore Office products.
- Export Outlook items to an Outlook Data File (.pst).
- Microsoft ends support in Office 365 for Outlook 2007 and 2010 clients.
- Outlook Updates applies to Outlook 2016, Outlook 2013, and Outlook 2010.
- Help for Outlook Web App.
- Computer Hope's Outlook Resources.
- HowTo-Outlook provides weekly tips.
- The OutlookAddressBookView displays the details of all recipients stored in the address books of Microsoft Outlook.
- Aid4Mail (from US$19.95) can migrate, archive and analyze the messages in all your email programs. It does this without modifying the original messages.
Moving To/From Outlook
- Import and export Outlook email, contacts, and calendar.
- Import email, contacts, and calendar from an Outlook .pst file.
- Exporting and importing mailbox content in Outlook.
- Import email account data from Outlook on Macintosh.
- G Suite migration for Microsoft Outlook (Google apps).
- Export and backup emails from Outlook to Gmail online (2009).
You may need to use a third-party import/export solution.
Dealing with "winmail.dat" Attachments
If you receive a message with an attached file called winmail.dat you probably will be unable to open it.
Invisible to Outlook Users
The winmail.dat is invisible to users of Outlook and Outlook Express (an obsolete email program), so such users may not know what you are referring to when you mention it to them.
Other email clients, like Thunderbird, The Bat!, or webmail programs can all send enhanced HTML-based email without any problems for the recipient. This issue is specific to Microsoft's email clients.
- Transport-Neutral Encapsulation Format (TNEF) gives a fuller explanation of this issue and the solution.
- MozillaZine discusses TNEF for Thunderbird and other Mozilla email programs and provides some solutions.
- Wikipedia's explanation of TNEF.
- Wikipedia's history of the various versions of Outlook.
Gmail now requires OAuth 2.0 sign-in which will affect all email software.
Thunderbird and The Bat! both support OAuth 2.0 authentication for Gmail accounts but you need to turn it on in your Gmail account settings (both the incoming and outgoing server).
Thunderbird 91.8.0, released 5th April 2022, converts the authentication method of Gmail accounts to OAuth 2.0 to help users comply with Google's requirement of OAuth 2.0 for Gmail logins. These changes are required by Google.
— Mozilla Support
However, changing the account settings is only the beginning.
You then need to give Google permission to allow your email software to access your Gmail account. Check your email program's support and forums for information specific to using Gmail and OAuth 2.0.
See the following for information on making the necessary changes:
- Automatic conversion of Google mail accounts to OAuth 2.0 authentication provides help for Thunderbird.
- Using OAuth2 with Thunderbird and Gmail.
- Set up Gmail with a third-party email client provides support for Microsoft Outlook and Apple Mail.
Gmail is now configured to use labels rather than physical mailboxes to sort your email. These should be configurable when using IMAP (Gmail is designed for IMAP).
Be sure to configure your Gmail IMAP settings in your email program to match the labels you've used in Gmail. You'll need to log into your Gmail account in a browser during the process of matching labels to your email program's IMAP mailboxes.
“All mail” includes the inbox label by default. Be careful when removing this. Non-existent labels may cause retrieval issues.
- Switch to labels from folders — Google Workspace Learning Center.
- Gmail Labels: everything you need to know.
Subscription Lists Broken
Gmail made changes that broke how subscription lists were dealt with. This created problems for people subscribed to lists.
Gmail changed how email subscriptions were sorted. The Primary category was designed so you could quickly find your most important emails easier.
Mail deemed less-important was moved into either the Social (Facebook notifications, etc.) or Promotions (bulk mail such as ads but also subscriptions, updates and more) categories.
Unfortunately, subscription lists and update notices were categorized as Promotions, along with “junk” ads.
How to Fix It
- Click on the Promotions tab and select messages you wish to go into your primary mailbox.
- Drag the selected message onto the Primary tab.
- A pop-up message will ask if you wish to do this for all future messages from the addressee of the dragged message. Say “Yes.”
- Continue to monitor the Promotions inbox to ensure that other messages aren't getting left behind.
Alternatively, you can turn off the new tabs completely by going to the settings, click on the Inbox tab and deselect the tabs you don't want to use (e.g., Promotions) then save the changes.
Gmail Spam and Email Programs
Gmail has a very effective spam filtering system — sometimes too efficient. To compound this issue, third-party email clients like Thunderbird and The Bat! are not permitted to download mail from Gmail's Spam folder.
To resolve this issue, you'll need to log into your Gmail account using your browser.
Go to the Spam folder then select all your legitimate email messages and click on Not Spam to train Gmail's spam filters to accept mail from these addresses.
You may need to continue to check the Spam folder over time so that Gmail improves its recognition of legitimate emails rather than labelling them as spam in the future.
- How to clean up your Gmail inbox with this mass delete trick.
- Gmail marks legitimate emails as SPAM! How to correct this?
Mac Mail Issues
These resources may help you to resolve Apple MacIntosh:
- Mac Mail App Support — Apple's support for the built-in Mail app that came with your Mac.
- If you can't send or receive email on your Mac.
- Import email account data from Outlook on Macintosh.