Email Software & Issues

Email Clients | Web-based Email | Dealing with Email Issues | Email Newsletters
See also: Web Browsers & Plugins

Email software and tips for dealing with email problems.

Email remains one of the most important forms of communications today. It is convenient and available on the go via your phone.

That said, you don't want to jeopardize your mail, your security or trade your privacy for ease-of-use.

Unfortunately, many desktop email clients are slowing or stopping development. The pickings are getting slimmer.

Stand-alone Email Clients

I strongly recommend a stand-alone email client that will meet your needs as your primary form of email communication — particularly you need to keep copies of important messages over the long term.

You can archive your mail on your computer without having to pay for increased storage on your ISP's server 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 (remember “@home” email addresses?).

Recommended Email Clients

I recommend the following stand-alone products, depending upon your requirements.

Thunderbird

Download Thunderbird

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.

Thunderbird is not recommended for those with high email volumes such as business users.

The Bat!

Download The Bat!

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.

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:

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.

Spam Control

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. Some add “*SPAM*” to the subject line which is annoying for false positives.

I've not determined an easy way to 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

Download Postbox

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.

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.

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.

There are also issues with licensing and user rights:

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.

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:

Whatever email client you choose, be sure to learn about security issues.

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Web-based Email

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:

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.

Because your mail is "in the cloud" you trade the convenience of any-where, any-time access for lack of privacy and security:

Gmail Changes Affect Subscription Lists

Gmail has created three new categories to sort your mail:

  • Primary;
  • Social; and
  • Promotions.

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

  1. Click on the Promotions tab and select messages you wish to go into your primary mailbox.
  2. Drag the selected message onto the Primary tab.
  3. 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.”
  4. 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.

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Dealing with Email Issues

winmail.dat Attachments | Importing/Exporting From Outlook Express | Outlook Resources
Reading Email Headers | Email Security Issues

Outlook Express is Obsolete

Outlook Express is installed as the default email program for Windows XP.
Do NOT use this program (uninstall it and move to another stand-alone email client or web-based email. See Importing/Exporting From Outlook Express.

Issues with Outlook/Outlook Express? Don't Blame the Recipient

Most of the issues in this section deal with problems with Outlook or Outlook Express:

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.

Disabling 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:

  1. On the Tools menu, click Options, click the Mail Format tab.
  2. 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:

  1. On the Tools menu, click Options, click the Mail Format tab.
  2. 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:

  1. On the Tools menu, click Options.
  2. Click on the Mail Format tab and uncheck the "Use Microsoft Word to edit email messages" box, then click OK.

Microsoft Documentation

Other Explanations

Third Party Solutions

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.

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Importing/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).

Here are a number of suggestions that can help you with this process.

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Outlook Resources

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:

Utilities for Outlook:

Moving to or from Outlook? These tips and guides will help you:

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Email Headers

If you are having issues with either getting an email or getting emails you'd rather not have (spam), you'll probably get asked to forward the messages with the full headers intact.

What are Headers?

Headers include the information at the top of the message like the subject, who its from, who its addressed to (TO: and CC:), the date it was sent. The information displayed and the order it is displayed in varies by program.

Full Headers

Full headers have a lot more information including the path taken by the message from the sender to you. It is this second set of information that allows the person you ask for help to determine how the message arrived in your mailbox and who forged it (most spam is sent using someone else's email address, perhaps your own).

Information Varies by Program and ISP

The sort of information captured by your email program depends upon what the designers of that program considered important (some can be configured to show more or less) as well as information that may be added by your ISP (Shaw, Telus, Rogers, etc.) Islandnet.com (strongly recommended) provides a great deal more about how mail is filtered through their powerful PEP (Personal Email Processing) system, including tools to help you avoid spam.

Viewing the Full Headers

To view the full headers depends upon the program you're using:

Other programs should have similar methods.

Forwarding Messages with Full Headers

To forward the message with full headers usually requires that you forward the message as an attachment. By queueing the message you can go to the Out box and check that the attached message has full headers before sending the message.

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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.

There is additional security information in the Preventing Unauthorized Access and Internet Security Vulnerabilities pages. You'll want to ensure that you are running current Anti-Virus Protection as well.

All trademarks, company names or logos used on this page are the property of their respective owners.

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Email Newsletters

As email has become widespread, many businesses and organizations have moved to sending out their formerly-printed documents by email. Among these documents are their newsletters and other notices. This works very well, but you must be aware of the differences between how email programs when you send these documents.

Your e-newsletters will be read using many programs on different operating systems. If your recipients are having difficulty reading your emailed newsletters, your message will not get out and it is going to reduce your subscriber base.

Keep it Private

Opt-in Addresses Only

If you don't want to generate resentment, you'll use an opt-in list where everyone specifically asks for your newsletter.

You can invite people to sign up for your newsletter on your website and in print copies of your newsletter or other documents. Be sure not to pre-select boxes giving authorization. This "presumed close" practice is sleazy (is that the reputation you want for your company?) and will not generate customer loyalty.

Opt-out Sucks — with Some Exceptions

Simply offering a way off your list does not in itself make your list opt-in (that's an opt-out list). One exception to this might be a club newsletter where it is made clear to the members that they will be receiving an email-based newsletter when they sign up.

BCC: Your Address List

Don't upset your readers by disclosing their email address to everyone else. Use BCC: to add all the addresses. If your email program insists on an address in the TO: slot, use your own. Learn more about proper email address etiquette.

Make it Accessible

HTML or Plain Text?

Not everybody can view enhanced (HTML) email messages or properly view encoded images (although this is pretty much the norm these days). You can offer the option to view the message in a browser, but this is risky for your recipients and is annoying for regular postings.

Be sure to either offer a plain-text newsletter or to design yours so that it can be read without the extra coding and images (don't use images to convey the message content). It is recommended that you test your messages on a variety of email clients and platforms (operating systems) so you can to catch these bugs before they come back to bite you.

Avoid Remote Images

Avoid including images with complex names stored on remote servers. Sure remote images save email bandwidth, but they'll need to be opened at some point and that may not work as expected in all mail programs. Is their inclusion so they can be used to track who opens the messages? Sleazy.

Colour and Backgrounds

Be careful when using backgrounds and colour schemes while developing your e-newsletter. Some colours may have unexpected emotional or cultural impacts as well as creating issues for those that have various forms of colour-blindness.

The following pages cover this in greater detail:

Backgrounds can also be rendered as page-after-page of nonsense text if the email program doesn't interpret it correctly or if the message or background information becomes corrupt during transmission or download. It is safest to use no background or to specify a neutral colour.

Problems with Outlook/Outlook Express

If you are sending out an email-based newsletter, it is very important that you either do not use a Microsoft email program, or that you ensure that you've taken care of the winmail.dat problem. Sending your clients large unusable attachments will simply annoy them.

Avoid Bandwidth Hogs & Incompatibilities

Downloaded Images

You may have noted that some newsletters use images that are downloaded from the server when the message is viewed. This saves bandwidth when sending the message, but can create a strain on your ISP's server (and your account bandwidth) if you aren't careful. Remember, every time someone opens the message, they'll be downloading these images (not just the first time) as will everyone they forward it to.

These downloaded images are also used by spammers to track messages they send for verifying email addresses and logging when the message is opened. Many email programs, like Thunderbird or Pocomail, deal with this by disabling the downloading of images until the viewer asks for them.

Attachment Issues

An alternative to self-contained messages is to attach a newsletter to the message. Be careful about your choice in the attachment format as you will want your viewers to be able to view the message.

You should make your decisions based upon your intended audience. In some cases MS Word may be more attractive to your viewers, and if layout is not extremely tight, the printer configuration issue may not matter. Be sure to test your message on other computers with different printers before settling on this solution.

Document Size Issues

If you are composing a newsletter in MS Word, be sure to resize images to fit before inserting them into the document. Resizing them in the document doesn't reduce the actual file size — an important issue when documents are intended for sending as attachments or posted on the Web. This is also true for documents that will later be translated into Adobe PDF.

Other References

There is a lot at stake when you start developing an electronic newsletter and there are people that specialize in their creation. Here are just a couple of places where you can go for more information:

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More About Related Issues

Protecting Your Online Identity

The following related pages offer more information about protecting your online identity:

Securing Your Computer

The following related pages offer more information about securing your computer:

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www.RussHarvey.bc.ca/resources/mail.html
Updated: February 27, 2014