Russ Harvey Consulting - Computer and Internet Services

Email Software & Issues

Clients | Web-based | Email Issues | eNewsletters
See also: Web Browsers & Plugins

Email remains one of the most important forms of communications today. It is convenient and now available “on the go” via your smart 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 pretty slim.

Stand-alone Email Clients

A stand-alone email client is a program on your computer that stores downloaded messages on your own computer.

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 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?).

IMAP Issues

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.

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 you either are charged more or the ISP may simply delete the oldest messages (often arbitrarily and without warning).

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.

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 ($59.99) and Home ($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:

  • 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.

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.

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

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.

  • 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 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).

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.

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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.

‘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:

  • 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 | Importing/Exporting | Outlook | Email Security

Outlook Express is Obsolete

Do NOT use Outlook Express, an obsolete product installed with Windows XP (also obsolete). See Importing/Exporting From Outlook Express.

Issues with Outlook? 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

  • 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

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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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).

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.

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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:

  • 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:

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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.

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.

Remote Images

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.

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

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www.RussHarvey.bc.ca/resources/mail.html
Updated: May 8, 2015

Email software and tips for dealing with email problems.

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 (not the reputation you want for your company) and will not generate customer loyalty.

The Canadian anti-spam legislation (CASL) came into effect on July 1, 2014 and has significant penalties for this practice.

The manner in which you request express consent cannot presume consent on the part of the end-user. Silence or inaction on the part of the end-user also cannot be construed as providing express consent. For example, a pre-checked box cannot be used, as it assumes consent.
CRTC FAQ about CASL

Opt-out Sucks

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.

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 depend upon 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.

Some companies that offer e-newsletter services provide their clients with information on who opens messages, who they forward them to and more.

This is great from a sales point of view, but kind of creepy. Email clients like The Bat! can prevent images from opening and provide a bit of privacy.

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 characters 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.

Outlook Has Issues

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 The Bat! or Pocomail, deal with this by disabling the downloading of images until the viewer asks for them.

Attaching Newsletters

An alternative to self-contained messages is to attach a newsletter to the message.

Since this forces people to open another document, an inconvenience to busy people, many may not bother.

Be careful about your choice in the attachment format as you will want your viewers to be able to view the message.

MS Word

While Microsoft Word is used by most businesses, not everyone has Word (although they may have LibreOffice or OpenOffice).

Your document may not display as expected if the printer settings are different on the viewing computer.

PDF

PDF locks the format into the document and the various PDF readers are free (and already installed on most computers), making it an excellent choice.

While many programs can create PDFs, be sure to ensure that the compression is good enough to provide the smallest document size.

Know Your Audience

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. This is also true for documents that will later be converted into PDF.

Other References

There is a lot at stake when you start developing an electronic newsletter. You might want to out-source the project or use a service like ConstantContact or MailChimp.

Start here when looking for more information:

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Related Resources

Related resources on this site:

or check the resources index.

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