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 is one of the most important forms of communications today. You want to select a program that will meet your needs, but don't want to jeopardize your computer's security or trade your privacy for ease-of-use.

Stand-alone Email Clients

As people move to smart phones and to webmail many desktop email clients are slowing or stopping development. Thunderbird is only the latest (July 2012) in a series of such announcements.

When it came out in 2004, Thunderbird's biggest competitor was Microsoft's Outlook. However, in the intervening years many if not most businesses and consumers have switched to webmail of some variety. Many also now use instant messaging and collaboration platforms instead of email.
— ZDNet

That said, I strongly recommend a stand-alone email client as your primary form of email communication — particularly you need to keep copies of important messages over the long term. It 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.

Recommended Email Clients

Pocomail and Barca have been my choices for a robust email program for people and businesses with heavier demands.

However, forum postings by Pocomail's creator in October 2011 indicated that Pocomail and Barca development has ceased. In February 2013 the Pocomail Forums ceased to work (an error message is displayed). More here….

Thunderbird

Thunderbird (free) is a powerful, yet easy to use, stand-alone email program that works great in conjunction with the Firefox browser.

Get Thunderbird specific-language dictionaries and other addons.
Thunderbird standard diagnostic.
Setting and Changing Email Passwords in Thunderbird (but also applies to Mozilla Suite/SeaMonkey).
MozillaZine articles related to Thunderbird is the best place to look for help.

Thunderbird's Future

Mozilla announced in July 2012 that a Mozilla email client “is not a priority” anymore. Later discussion was more encouraging:

Nothing will change for individual and enterprise users: Mozilla will continue to support and maintain Thunderbird. To be more specific, Mozilla will no longer focus on developing innovations for Thunderbird but will keep it safe and stable. Mozilla will also provide all the infrastructure required for new, community-developed features to be integrated in upcoming Thunderbird releases.
— Mozilla Blog

Postbox

Postbox (US$9.95) 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).
Try Postbox free for 30 days to see for yourself.
Postbox Add-ons provide a calendar, import/export tools….
View the blog for news, updates and hints.
Volume discounts start at only 2 licenses. License agreement.

Importing Mail, Contacts and Settings

Postbox offered to import settings from my Thunderbird right after the initial install, possibly because Thunderbird is present (I use it to support clients running Thunderbird). After Postbox was running the Import menu only offered to import from Outlook, Outlook Express and Windows Live. Presumably, it discounted Thunderbird as I'd not imported its settings at the start.

There appears to be no way to import the multiple accounts, mail and contacts from Barca (and presumably Pocomail). I just have too much mail to simply abandon it and start afresh.
I've downloaded an Import/Export addon but it will take some working through how it will see Barca's mailboxes if it is at all possible.

I have yet to see any other option except manual setup. I have far too much important mail to simply abandon Barca and start afresh. Several of my clients are in the same position, so I'll continue to work though the possibilities.

Alternative Email Clients

No Native Email Program for Windows 7

There is no native email program for Windows 7 (Vista has Windows Mail) so you need to use webmail or find a new email program.

You may find information on how to enable Windows Mail on Windows 7, but these changes will create problems with Windows Update.

Email Clients Overview

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.

DreamMail

DreamMail (free) is a powerful stand-alone email program designed to handle multi-user and multi-email accounts. Originating in China, the English version is available through the DreamMail European Community for Windows XP/Vista/7.

Learn more….
See the Download page for available language versions (limited at this time) and system requirements.
The DreamMail Community Forum is the best place to look for help.

I'm currently evaluating DreamMail as a potential email client. It appears to be very powerful and may provide options that are harder to implement in Thunderbird for demanding users. However, given the issues with high-level hacking coming from China, I'm not sure this program can be trusted

Microsoft Outlook

Microsoft Outlook is usually installed as part of Microsoft Office, but can be purchased separately. It runs on Windows XP or better.

Outlook is routinely used in the business community, particularly in large corporate environments where capabilities for inter-office communication and project coordination are needed.
Home users may find some of the advanced features useful but it is not recommended for novice users because the configuration is more complex.
Be sure to use a currently-supported version of Outlook (one that continues to see updates from Microsoft).
InfoWorld reports that Outlook 2013 license terms are “draconian, obtuse — and documented incorrectly on Microsoft's own website.”
Backing up Outlook 2010.
Outlook users need to be aware of the issue that winmail.dat attachments can present to non-Outlook users.

Microsoft Outlook is not included in the recommended list because of the security vulnerabilities generated by Microsoft's tight integration between their products. While convenient, any vulnerability in one component transfers to another (particularly problematic since this includes the Windows operating system).

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.

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 Windows XP, but is now unsupported and obsolete. It should be uninstalled.
Eudora classic, though once popular, is now unsupported and obsolete. It should be uninstalled.
Better alternatives include Thunderbird (free) or Postbox (US$9.95).

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

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Web-based Email

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 with Windows 7 (and Windows 8 appears to be following the smart device trend). 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:

your mail is read to provide advertising based upon its content;
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.

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Dealing with Email Issues

winmail.dat Attachments | Importing/Exporting From Outlook Express
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.

This Affects the Recipients of Your Messages

Most of the issues in this section deal with problems with Outlook or Outlook Express. This will affect those you send messages to. Don't blame the other email programs — it is the sending program that is creating the problem.

If you distribute email newsletters your messages will be read using many programs on different operating systems. If your recipients are having difficulty reading your emailed newsletters, it is going to reduce the effectiveness.

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:

Direct link to this winmail.dat section.

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:

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.

Microsoft Documentation

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.

Other Explanations

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.

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Importing/Exporting From Outlook/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.

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.
Resources For Outlook Express and MS Outlook How-to Articles are indexes to Microsoft Help & Support pages for the issues listed there.
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.
Mailbag Assistant (US$29.95) can search, organize, analyse and archive the messages in all your email programs. It is also useful as an intermediary tool to transfer messages from one mail program to another.

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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:

Thunderbird View > Headers > All (Headers > Normal is the default)
Pocomail or Barca View > Message Headers Display > Show Full Headers (Show Short Headers is the default)
Outlook Express Right-click on the message in the list of messages and select Properties. Click on the Details tab to view the full headers.

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.

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 PocoMail, Barca and Thunderbird disable the downloading of images by default to protect you from this risk.)

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.

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.

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:

Understanding Color and Accessibility.
Color Vision 1 in 12 people have some sort of color deficiency.
Colour Meaning—what various colours signify.
Colour Symbolism.

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.

While Microsoft Word is used by most businesses, not everyone (including many non-profit organizations) have Word. You should also take into consideration that the format changes to fit the printer installed on the viewing computer. Free Microsoft viewers are relatively unknown, with few people using them.
Adobe® Acrobat® locks the format into the document and the Adobe Reader is free (and already installed on most computers), making it an excellent choice. While there are free tools to create PDF files for distribution, Acrobat® does the best job of ensuring the look you want with the smallest file size for efficient distribution.

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:

Email Newsletters: Surviving Inbox Congestion.
How to Code HTML Email Newsletters for the more technically-adept.
Email Newsletter Usability has a summary or you can download the entire 544 page report for US$398.

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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: May 6, 2013