How do I get "Send To" to work with Hotmail? Or Gmail? Or some other web-based email?

As far as I can tell so far, you can’t. I could be wrong and I hope that I
am, but this appears to be something that quietly got worse in Windows 7.

There are work-arounds, but they really do side-step the issue rather than
actually solving it.

I’ll describe the problem in more detail and list some of the possible
work-arounds.

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The ‘default program’ problem

Windows has the concept of a “default mail program” that it uses when you instruct some Windows utility to send mail. The best example is Windows Explorer’s own menu item where if you right-click on most files, you find a “Send To” option that includes “Mail recipient” as one of the possibilities. Click that and Windows fires up the default mail program to automatically compose a new message and attach the specified file to it.

Other applications often do similar things (including a “Send mail” option without needing to be told how) simply by making use of Windows default mail program.

Here’s the catch: your web browser is not a mail program.

If you use Internet Explorer, Firefox, Chrome, or any other web browser, you’re not actually using an email program. You’re using that browser to access your email in the form of web pages provided by the email service’s web servers.

It’s convenient, but it’s not a program, and I’m not aware of a way to make Windows 7 treat it as if it were.

Thus, you can’t configure it to be your default mail program.

But it used to work

In the past, there were ways – sometimes utility programs, sometimes registry hacks, and sometimes just pure magic – that could allow you to specify Hotmail or Gmail or whatnot as your default email program.

From what I’ve found so far, they no longer work – either with Windows 7, newer versions of Internet Explorer, or both. In fact, some of the utilities that used to exist seem to have disappeared.

Workaround 1: Switch to using a PC-based mail program

This is one extreme. Basically, get and install a PC-based email program like Windows Live Mail, Thunderbird, Outlook, or any of perhaps hundreds more. Almost all of them will automatically set themselves as the default mail program on installation, or ask if you’d like them to.

Configure that program to access your email and begin using that instead of the web-based interface.

The good news is that this makes backing up your email (something I strongly recommend anyway) much easier and insulates you from random user interface changes on the Web.

If your email provider supports it, choosing IMAP instead of POP3 means that you can access your email either via the web or via your internet-connected PC. Pretty handy overall.

The bad news is that if you can only use POP3, then email is downloaded and stored on your PC, meaning that you can only access it from your PC.

But using a desktop email program for this purpose might perhaps be the safest approach overall, as it’s the most common way for people to access email in general.

It’s just not what everyone wants.

Workaround 2: Use PC-based email only for PC-based requirements

Keep using your web-based email – don’t change a thing.

But…

Also download and install a PC-based email program. Configure that email program only to send from your email account and never, ever to receive.

That way, you’ll continue to access your email via the web as you do now, but if you want to use a feature like “Send To -> Mail recipient”, you can – and only then will the email program that you’ve installed on your PC be used.

As I said, the “trick” is to make sure that the program never downloads email. Depending on the program, that might include some or all of:

• Turning off automatic “Check for new mail on start”.

• Turning off periodic “Check for new mail”.

• Turning off “Check for new mail on send”.

• It could even mean purposely misconfiguring the POP3 or IMAP server name so that any attempt to receive will always fail.

Why is it so important to disable receive in this case? If you’re only looking at your email on the web, then if your PC-based email program accidentally downloads a message to your PC, you may never see it.

Use the steps that the features replace

Most of the time, features like “Send To -> Mail recipient” are simply shortcuts for things that you can do a different way. For example, “Send To” in Windows Explorer on some file is really just a shortcut for the following sequence:

• Compose a new message in your email program.

• Attach the file to that new message.

• Add some standard text to the body of the message (optional).

So, instead of using “Send To”, just go to your web-based email and perform those steps manually. It may not be as convenient, but it works.

Next steps

If you know of a reliable, supported solution for Hotmail and/or Gmail that works in the latest versions of the Internet Explorer, FireFox and Chrome browsers (please make sure that it’s reliable and supported and that it actually works), then please do leave a comment below. I’m actually somewhat surprised that things are in this state and hope that I’ve overlooked something.

In the mean time, if you’re considering the switch to a desktop email program, have a look at What are the pros and cons of web-based email over desktop email? for a discussion of the various … uh … pros and cons.

If you’re dealing with older versions of Windows and/or browsers, have a look at How do I change the “mailto:” or default mail program? for the way things used to work – perhaps an old solution there will work for your case.