I couldn't think of a better title for this question, but please don't jump to conclusions - I don't really want to point a gun at my users heads!
I have a site that works well with the modern browsers like IE9+, FF12+, or Chrome. Due to the lack of HTML5 support (specifically some canvas related issues) the site doesn't work in older browsers, like IE8, for example.
The site is a part of a prepaid service, the users are warned about these constrictions before they pay, and yet there still are users that buy the service while having these old browsers on their computers.
From one side to support those means to fully recreate the site in Flash or Java, for example. That means lots of work for a relatively small (up to 15%) percent of my target audience.
From the other side I don't want to "disappoint" them by bluntly stating "Your browser is too old", I want to give them an interesting feedback, visually and/or verbally, that will make them really want to upgrade. The best idea I come with is to show them the video of the working site, but it seems too heavy and boring.
Any suggestions? Thanks.
UPDATE:
It seems from a short user survey that I did, that users definitely prefer to install a plugin and not to upgrade. Therefore I am going to accept the Chrome Frame answer.
I want to thank you all for a very interesting discussion, I have learned a lot and got a lot of inspiration from it.
Answer
Updated Answer - March 2013
Since this answer was posted on November 2012, Google has discontinued this plugin. While it might still work as of today (March, 2014) there is no guarantee of it working in the future. As of January 2014, support for Chrome Frame is discontinued:
http://googlesystem.blogspot.com/2013/06/chrome-frame-discontinued.html
Given these factors we’ve decided to retire Chrome Frame, and will cease support and updates for the product in January 2014. If you are a developer with an app that points users to Chrome Frame, please prompt visitors to upgrade to a modern browser. You can learn more about these changes in our FAQ.
If you’re an IT administrator you can give your employees the full capabilities of a modern browser today, even if you depend on older technology to run certain web apps. Check out Chrome for Business coupled with Legacy Browser Support, which allows employees to switch seamlessly between Chrome and another browser. Chrome is secure, stable and speedy, and runs on all major desktop and mobile OSs. IT admins can also configure 100+ policies to make Chrome fit their needs.
The blog post points to Chrome for Business with support to automatically open specified web-pages in alternate browsers
Original Answer
Key point that hasn't been mentioned: Some people CAN'T upgrade.
At work, I'm forced to IE8 (Upgraded from IE6 late last year, early this year).
Do what Basecamp does. Push IE 6/7/8 into Chrome-Frame : 
You can't "Force" everyone to upgrade. Some users don't have the option. Give them options to use within their restrictions (Work Restrictions, lack of admin rights, etc.).
Work restrictions prevent upgrading certain applications. This app only works with IE8. That app crashes on Adobe 10+. XPSP3 breaks this. SQL Server patch #12345 breaks that. I heard recently that the main restriction to upgrading isn't convincing people. It's paying the bill to upgrade Foo to work with Shiny-New Bar.
(Granted, at work I have admin so I use Chrome. BUT I CAN tell other users to use IE8 + Chrome Frame, for those who can't/won't stray outside of "supported" boundaries.)
How can I enable Google Chrome Frame for my site?
You make your pages work with Google Chrome Frame by adding a single
tag, like this:
Google Frame Installed + That tag = Chrome Engine used inside IE6-9. They keep IE6. You stop supporting IE6. Win-Win.
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