Email Software & Issues
Email remains one of the most important forms of communications today. It is convenient and is now available “on the go” via your smart phone.
You don't want to jeopardize your mail, your security or trade your privacy for ease-of-use.
From One Computer to Mobile
Traditionally, people had only a single computer and downloaded all message to that one computer, storing important messages forever using POP/SMTP settings. However things have changed.
Today people want copies of their messages on their computer, laptop, smartphone and tablet so they set up IMAP, a method of connecting to your ISP that mirrors the messages on the server on all IMAP-connected devices.
Most ISPs simply give people what they ask for, without explaining the issues or potential problems.
IMAP Not Great for Archiving
However, there are important issues with IMAP that you should understand:
- Deleting messages with IMAP on any of the connected devices will remove it from both the server and ALL devices connected to that account with IMAP.
- Most email accounts have limits on how much you can store on their servers.
- Once you pass that limit the ISP may simply delete the oldest messages or “bounce” incoming messages (often arbitrarily and without warning).
- You can purchase extras storage, but some ISPs limit the amount of space you can purchase even though the cost of storage has greatly increased.
Stand-alone Email Clients
A stand-alone email client is a program on your computer that stores downloaded messages on your own computer.
Unfortunately, many desktop email clients are slowing or stopping development. The pickings are getting pretty slim.
You Need Archive Capabilities
I strongly recommend a stand-alone email client for your primary form of email communication, particularly you need to keep copies of important messages over the long term.
That way you can archive your mail on your computer without having to pay for increased storage or suddenly finding out that you've lost all access to your mail if your ISP goes out of business or changes their email hosting service.
For example, many of us remember “@Home” email addresses that were used all across North America but later failed.
Set Up a Primary non-IMAP Account
Use your primary account (using POP/SMTP*) for your important email or where you may want to archive messages over the long term. The primary account should NOT be an IMAP* account.
Use IMAP on Secondary Accounts Only
Use IMAP only on a secondary email account for messages on all your portable devices (e.g. smartphones, tablets, secondary laptops).
You can still access the mail on your primary account on your remote devices provided this account is configured for POP/SMTP. You'll be able to access NEW message as long as the primary computer has not accessed them.
*IMAP, POP and SMTP are email protocols and important only when configuring email retrieval. Once setup, email will be managed transparently if the settings are correct. Learn more….
Recommended Email Clients
I recommend the following stand-alone products, depending upon your requirements.
Thunderbird (free) is a powerful, yet easy to use, stand-alone email program that works great in conjunction with the Firefox browser.
Thunderbird works great for many home users those with simpler demands. It automatically sets up for Gmail and other such cloud-based email so you don't have to log onto via your browser to view and send your mail and will allow you to archive messages in separate folders for long-term storage independent of the server.
- Mozilla announced in July 2012 that a Mozilla email client no longer a priority but support continues although not at the previous pace (or as frequent as Firefox).
- Installing Thunderbird on Windows, Mac or Linux.
- Get Thunderbird specific-language dictionaries and other addons.
- Thunderbird standard diagnostic.
- Setting and Changing Email Passwords in Thunderbird.
- MozillaZine articles related to Thunderbird is the best place to look for help.
Thunderbird is not recommended for those with high email volumes such as business users.
The Bat! Professional (US$59.99) and Home (US$26.95) are both flexible, secure email programs and highly recommended for advanced users requiring more customization and handling of their email. It has an internal HTML viewer (for security), advanced message handling, OpenPGP encryption and more.
- Support for the Exchange Web Services (EWS) protocol makes The Bat! a secure, customizable and cost effective email client alternative to MS Outlook (version 7).
- Security and a speed boost are two of the benefits of running the 64-bit version of The Bat! (released with version 6.7.20).
- The license agreement allows a individual user to install multiple copies provided only one is active at a time (e.g. on your desktop and laptop). Corporate users need to obtain a site license and the rules are different.
- Screen shots of the mail interface, message editor window, sorting office and address book.
- Differences between the Home and the Professional Edition.
- The Bat! Voyager provides secure portable email via a USB drive. Free with The Bat! Professional Edition.
- The Bat! Tips and Tricks provides a quick link to using features.
I was particularly impressed with the level of automated message handling. In fact there are so many features that it has taken me some time to learn to use them (and how to configure them) but when enacted they provide powerful tools for organizing and handling your mail. For example:
- The Sorting Office provides for filters and can be set up as general or separately for individual accounts.
- Folders can be configured to auto-delete messages based upon the age (e.g. a price list that updates weekly) or by number of messages (to avoid overloading your computer's system).
- You can limit the size of the messages that are downloaded (retrieving only the headings for larger messages) such as on your laptop where you don't need the full message and want to save space on your hard drive.
- The Bat! blocks external images by default, but controls image display on a per-sender basis, listing the image sources and allowing you to accept images from all the related sources or simply allow them for the sender's domain or on a one-time basis.
- The Bat! provides for better HTML-based templates for New Message, Reply and Forward for each account and can be configured for Confirmation messages to put in Outbox, Send immediately, Edit or Ignore (I use Ignore to disallow a reading confirmation receipt).
- The Bat! has a mailbox analyzer that will look for consistencies in email and automatically create new folders and filters for larger volume senders.
I strongly recommend that you configure The Bat! to use its own viewer rather than the newer option to use the system's viewer (Internet Explorer) for security reasons.
One weakness in The Bat! is spam control. There are various third-party addins, but you'll need to experiment to see what works for you.
I purchased AntispamSniper for The Bat! ($19.95) following the trial period.
Some of the others added “*SPAM*” to the subject line which is annoying for false positives as it wasn't easy to remove (AntispamSniper did).
I've not determined an easy way to manually remove this added text (the ability to edit the subject line was a feature that I found very useful in Barca). This forum post mentions one work-around: drag the message to the Outbox, edit it, then drag it back.
Use Internal HTML Viewer
I strongly recommend that you configure The Bat! to use its own HTML viewer rather than the newer option to use the system's viewer (Internet Explorer) for security reasons. Look in Options ⇒ Preferences ⇒ Viewer/Editor ⇒ HTML Viewer and select “Use The Bat!'s HTML viewer” and change the External images download control to “According to The Bat! rules.”
Postbox (US$9.95) may provide a Thunderbird alternative to those looking for something similar but with more features. It is a powerful email program which provides faster response times and has great features including integration with Dropbox, social media, Gmail and Google Calendar.
Your email, any way you like it.
- Windows and Mac versions (system requirements).
- Postbox Addons provide a calendar, import/export tools….
- View the blog for news, updates and hints.
- Volume discounts start at only 2 licenses. License agreement.
Pocomail and Barca have been my choices for a robust email program for people and businesses with heavier demands. These programs still work, even on Windows 8, but development has ceased. More here including help transferring messages to The Bat!.
Alternative Email Clients
Wikipedia's Comparison of Email Clients gives a good overview of the broad range of email clients including their release history as what operating systems, protocols and authentication methods they support. Most link to additional Wikipedia pages with additional information.
- Becky! Internet Mail (US$40.00) supports and has numerous features.
- Current Windows versions are supported.
- You can create not only multiple mailboxes but also create multiple profiles for each mailbox — very flexible mailbox management for people with multiple email accounts.
- The Beckymail! Yahoo! support group proved to be very responsive and helpful.
- My main concern is that it uses Internet Explorer to display HTML messages — something that even Outlook no longer does because of the security vulnerabilities (see my assessment of IE).
- DreamMail (free) is a powerful stand-alone email program designed to handle multi-user and multiple email accounts.
- Originating in China, the English version is available through the DreamMail European Community for Windows XP/Vista/7.
- It appears to be very powerful and may provide options that are harder to implement in Thunderbird for demanding users. However, I'm concerned about the privacy and safety of user data.
- The DreamMail Community Forum is the best place to look for help.
- Opera Mail (free) is a lightweight, customizable mail client.
- Current Windows versions are supported.
- Opera Mail used to be included as part of the Opera browser, but is now a separate install.
- The Opera Mail Tutorial provides help in mastering this program's features.
- Windows Mail was included free with Vista, but Microsoft didn't provide any email program with Windows 7.
- Microsoft took what they learned developing Windows Mail and updated their webmail services instead.
- While it is possible to enable Windows Mail on Windows 7 (most of the files are still there) these changes will create problems with Microsoft Update.
- Windows Live Mail (free) is part of online-based Windows Essentials.
Microsoft Outlook Not Supported
Microsoft Outlook is routinely used by business and governments, particularly in large corporate environments where capabilities for inter-office communication and project coordination are necessary.
If you decide to move to Outlook, be aware that I cannot provide the level of support I can with my recommended programs. I neither use nor recommend Outlook. It has given me more than its share of headaches and has left a bad taste in my mouth.
If you're tied into an organization or office that uses Outlook and you're familiar with that program, be sure to verify that you'll have help when problems arise.
- Be sure to use a currently-supported version of Outlook (one that continues to see updates from Microsoft).
- Home users seldom need or can use the elements demanded of Office in these environments unless they are tied into them.
- Recovery from a computer crash can be a nightmare without a current backup of the Outlook.pst file.
- Microsoft's tight integration between their products generates security vulnerabilities that can transfer between Microsoft products and Windows.
- In corporate environments, server backups of key files, sophisticated firewall systems and other measures can minimize these risks, but this is difficult for non-technical folks to emulate.
- Outlook users need to be aware of the issue that winmail.dat attachments can present to non-Outlook users.
There are also issues with licensing and user rights:
- Microsoft is moving towards Outlook.com and Office 365 to compete with Google Docs and Gmail.
- InfoWorld reports that Outlook 2013 license terms are “draconian, obtuse — and documented incorrectly on Microsoft's own website.”
- While Office 365 offers use on multiple computers (including Apple) it requires an annual fee and the default storage is in the cloud, NOT on your computer.
- A monthly or annual fee (like Adobe's Creative Cloud) is attractive to the bean counters. Microsoft, like Adobe, could stop offering a stand-alone product at any time.
See Outlook Resources for help with Outlook including backing it up, moving to or from Outlook and other helpful information.
Obsolete Email Programs
Outlook Express & Eudora Not Recommended
Programs where development has stopped and maintenance updates are not provided are not recommended. Such programs put your computer and data at risk.
- Outlook Express is automatically installed with the obsolete Windows XP. It should be uninstalled. See Importing/Exporting From Outlook Express.
- Eudora classic, though once popular, is now unsupported and obsolete. It should be uninstalled.
- Better alternatives include Thunderbird (free) or Postbox (US$9.95).
Exporting Mail, Contacts and 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 (like Thunderbird) will import this information from the most common current programs and even a few of the older ones.
However, many (like Pocomail and Barca) might need an intermediary program:
- Postbox has an Import/Export addon. Your mileage may vary.
- Aid4Mail looks more promising. It costs $19.95 US for home users; $39.95 US for professionals and organizations.
Whatever email client you choose, be sure to learn about security issues.
Web-based email is a server-based service where email stored on an external server (remote computer). Unlike email clients you no longer have control over your stored mail and unless you've downloaded it onto an email client it could disappear without warning. Be sure to use strong passwords to protect your account.
Web-based email programs have become much more commonly used as people moved to using multiple devices, particularly mobile devices to keep connected. The emergence of reasonably-priced laptops then "smart phones" has prompted the need for access to email while on the go.
As part of this trend, Microsoft doesn't include a built-in email client starting with Windows 7. The default option for these users is Windows Live, but any of these (and other) web-based email solutions are available:
- StartMail ($59.95 per year) provides an alternative
- Google's Gmail (Missing Mail? See Gmail changes affect subscription lists).
- Yahoo! Mail.
- AOL Mail.
Most internet service providers (ISPs) provide some sort of access to your email via a web browser. Here's some common local providers:
A Note About Webmail Weaknesses
Webmail services like Gmail, Windows Live (Hotmail) and Yahoo! have issues beyond what you experience with traditional stand-alone email clients.
‘Free’ email services like Gmail, Yahoo! Mail, and Hotmail come at a high price: your privacy. The fine print lets them search every message you send and receive for profit-generating keywords. They even keep their own copies of your deleted messages and your attachments. — StartMail — What's wrong with free email services?
Because your mail is “in the cloud” you trade the convenience of any-where, any-time access for lack of privacy and security:
- Your mail is “read” (including private or confidential messages and attachments) to build a profile of you for advertising and other purposes;
- even deleted messages are retained forever;
- the major carries caved years ago and provided back doors for the NSA;
- all your mail is constantly available to hackers looking for accounts with weak passwords (and account recovery tests that are often based upon information you or others have posted on social media networks like Facebook); and
- ownership of your information in the cloud is often reverted to the host company.
The companies that routinely gather your “metadata” would NEVER allow anyone to do the same with theirs — at any price.
Gmail Changes Affect Subscription Lists
Gmail has created three new categories to sort your mail:
- Social; and
This change helps to separate the more important mail from the Social (Facebook notifications, etc.) and Promotions (bulk mail such as ads but also subscriptions, updates and more).
It is this last category that you might find problematic as it can include email subscriptions which you want, not just “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.
Dealing with Email Issues
Obsolete Email Programs DangerousDo NOT use obsolete email programs like Outlook Express or Eudora.
Issues with Outlook? Don't Blame the Recipient
Most of the issues in this section deal with problems with Outlook or Outlook Express:
- winmail.dat Attachments are generated by both Outlook and Outlook Express but affect third-party email programs.
- Outlook Resources can help you deal with Outlook issues.
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/Outlook Express Users
The winmail.dat is invisible to users of Outlook and Outlook Express, so such users may not know what you are referring to when you mention it to them.
Other email clients, like Thunderbird, Pocomail, 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.
I recommend referring them to the documentation on this page so they can view an explanation and provide solutions. Click on the link below to have a new tab or window that opens directly here:
winmail.dat is a Microsoft Format Issue
Microsoft email clients (particularly Outlook), use the proprietary TNEF to encode the enhanced (styled) portions of the message and sometimes attachments are encoded using TNEF.
If you have difficulty opening a messages sent by Outlook but don't see the winmail.dat attachment, it is still possible that TNEF is the issue.
TNEF provides special features which makes it useful within a network where all members are using Outlook, but this can create display issues for non-Microsoft email programs.
Determining Your Version of Outlook
The solutions in this section vary by what version of Outlook you are using. Check Wikipedia for a history of the various versions of Outlook. It is strongly recommended that you do not use older versions of Outlook.
You can click on the Help menu then select About Outlook to determine what version you are using. Corporate users can contact their IT department for assistance.
A Plain-Text-Only Solution
The easiest solution depends upon the person re-sending the message as a plain-text message. Any other formatting (including Rich Text Format, enhanced (HTML) or messages composed in MS Word) will create this problem for non-Outlook users unless you disable TNEF.
In the following section you need to know what version of Outlook you're using because Microsoft changed its approach in Office 2003 (XP) and again with Office 2007.
For Microsoft Office Outlook 2007 or later follow these steps to turn off TNEF:
- On the Tools menu, click Options, click the Mail Format tab.
- In the Compose in this message format list, click Plain Text or HTML, and then click OK.
For Microsoft Exchange users Microsoft provides a more technical solution based upon external domains that may help your IT department determine a solution for all addresses external to your network.
For Microsoft Office Outlook before 2007 follow these steps to turn off TNEF:
- On the Tools menu, click Options, click the Mail Format tab.
- In the set the Send Format to either Plain Text or HTML. Do not select Rich Text format and be sure that you uncheck the "Use Microsoft Word to Edit Email Messages" box, then click OK.
Users of earlier versions of Outlook (97/2000) should simply send the message as plain text as any other formatting (including Rich Text or HTML format as well as messages composed in MS Word) will create this problem for non-Outlook users.
It is strongly recommended that you do not use older versions of Outlook — upgrade to a currently-supported version or move to a recommended email client.
Disable MS Word as Email Editor in Outlook XP or 2003
Unless you are exclusively sending messages within an internal department, Outlook 2002 (XP) and 2003 users will want to disable Microsoft Word as your default email editor because anyone not using Outlook or Outlook Express may be unable to read your message (or not as you intended).
To disable Microsoft Word as your default email editor in Microsoft Outlook:
- On the Tools menu, click Options.
- Click on the Mail Format tab and uncheck the "Use Microsoft Word to edit email messages" box, then click OK.
- Description of Transport Neutral Encapsulation Format (TNEF) in Outlook 2000 gives a fuller explanation of this issue and the solution.
- How email message formats affect Internet emails in Outlook.
- How to Prevent the Winmail.dat File from Being Sent to Internet Users for Microsoft Exchange Client users.
- 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.
Third Party Solutions
- Eolsoft's Winmail Opener (also available on Download.com) allows you to view and extract contents of TNEF messages. Free.
- WMDecode for Windows is a time-limited free utility to recover the information in winmail.dat files. You can re-download the file again later, or purchase the program for US$10.
- TNEF's Enough is a solution for Mac OS 9 and X users.
- SourceNet's TNEF Documentation includes a solution for Linux users.
Why it Matters
As you can imagine, most people will simply ignore your message or fret over their inability to view the winmail.dat attachment. Take a look at the suggestions in the Email Newsletters section for some ideas if you are sending out regular updates of any kind to a variety of people.
Exporting From Outlook Express
Outlook Express has a proprietary binary format that makes it difficult to extract email addresses either for archival purposes or to move your mail to a new program (recommended as OE is obsolete).
This section is intended to help you move from an obsolete and dangerous email program to an acceptable alternative.
Here are a number of suggestions that can help you with this process.
- Thunderbird can import address books, mail and settings. You can then use MozBackup, a freeware program, to create backups of your Thunderbird (and Firefox) profiles, including your mail, favorites, contacts, etc.
- The Inside Outlook Express is a site with information for troubleshooting and optimizing Outlook Express and includes FAQs, tools and known bugs.
- How to export email messages from Outlook Express into Outlook.
- You can use a utility like DBXtract to extract the messages from Outlook Express's dbx mailbox files. This utility is also useful for recovery of corrupted mailboxes. Be sure to read about potential problems with this process.
- Aid4Mail MBOX Converter (free edition) converts mbox-type mailboxes to EML files.
- Aid4Mail (from US$19.95) is an easy-to-use migration tool that can also archive mail.
Outlook has been the primary email client used by business and government for many years but is not as widely used by consumers because it is both complex and isn't aimed at consumer requirements.
Backing Up Outlook:
Having difficulties with Outlook? Try these resources:
- Support options for Microsoft Outlook 2010 and 2007.
- Search the Outlook Community postings for answers.
- Help for Outlook Web App.
- Computer Hope's Outlook Resources.
- HowTo-Outlook provides weekly tips.
Utilities for Outlook:
- 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 or from Outlook? These tips and guides will help you:
- How to export email messages from Windows Mail & Outlook Express into Outlook.
- Exporting and Importing Mailbox Content in Outlook.
- Google Apps Migration for Microsoft Outlook.
- The Export and Backup Emails from Outlook to Gmail Online.
- Export Email Addresses from an Outlook Folder.
- Aid4Mail (from US$19.95) is an easy-to-use migration tool that can also archive mail.
- Aid4Mail MBOX Converter (free) can convert between MBOX-type mailboxes and EML files.
Email Security Issues
Email programs have a number of recognized vulnerabilities which will depend upon the program and the platform (operating system) you are running it on. Those that wish to avoid spam (unsolicited junk email) should avoid software with these challenges.
Internet Explorer for Viewing Messages
Some Windows email programs use Internet Explorer components for displaying images and HTML (styled) messages. These programs are subject to the same vulnerabilities that Internet Explorer has.
If a remote image (one not attached to the email, but downloaded from the sender's server) is automatically displayed you risk the fact that the sender might be tracking whether the image is downloaded to your computer.
Some spammers use an identifiable image to determine which users actually open the mail in order to verify whether an email address is valid and if the message is read.
More recent email programs such as The Bat!, PocoMail, Barca and Thunderbird disable the downloading of images by default to protect you from this risk.
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Updated: August 7, 2015