If you send URLs to contacts using your e-mail program, you may have an issue where the receiving client breaks really long URLs. For instance, if you were trying to send a URL for a site like this one:

http://www.amazon.com/gp/product/B000BI5KV0/ ref=amb_link_4263902_/002-5510588-1062447

You might find that your recipients are unable to click on the link in their e-mail program. That’s because many e-mail programs will do what I did above—break really long “words” (for that’s all a URL is to them) into multiple rows. Typically when this happens, only part of the URL will show up as a clickable link. When this happens, your recipients will get a “page not found” message when they try to load the URL—because the browser will only receive that portion of the URL that showed as clickable. So how do you avoid this problem? There are a few alternatives, depending on your personal preferences. (Note that there are other ways to do this from your browser, but this is a tip about using your e-mail application, not your browser.)

Apple’s Mail app

If you use OS X’s built-in Mail program, and you send e-mail in rich text format, the easiest solution is to use the Edit -> Add Hyperlink menu item. First copy the long URL from your browser to your clipboard. Next, open a new e-mail message, and make sure it’s in Rich Text format (Format -> Make Rich Text). When you reach the spot in your e-mail where you’d like to use the URL, type in a short phrase describing the URL instead — March of the Penguins , for instance, for the above Amazon link. Now select that phrase and choose Edit -> Add Hyperlink and then choose Edit -> Paste (Command-V). When you click OK, you’ll see your phrase has been underlined, indicating that you’ve created a clickable hyperlink:





The plain text method

If, like me, you try to stay away from rich text e-mails, the simple thing to do is to surround your URL with angle brackets, like this:

<http://www.amazon.com/gp/product/B000BI5KV0/ref=amb_link_4263902_/002-5510588-1062447>

URLs enclosed in angle brackets should still be clickable—even if the e-mail client inserts a line break for formatting purposes. How come? Because back in 1998, the Network Working Group of the Internet Engineering Task Force (IETF) wrote this document, which describes a generic syntax for Uniform Resource Identifiers (URIs, of which URLs are a specific form). In the document, the working group describes how URIs enclosed in angle brackets should be parsed when the use of white space (such as line breaks) is required for formatting purposes. Any e-mail client that follows these guidelines should display a clickable link, even if the line is wrapped.

Unfortunately, you may still find some e-mail programs that break URLs within angle brackets. If that’s the case, and you’re hard set against sending rich text e-mails, you’ll probably need the next option.

Recode the URL

To prevent line wrap, the final option is to use a website to convert that long messy URL into a short one. TinyURL is probably the best known of these, though there are many others. Load the TinyURL website in your browser of choice, paste your long URL into the input box, and click the Make TinyURL button. Again using the above link, the TinyURL version is simply http://tinyurl.com/27ghfn, which will fit without wrapping in nearly any context.

For those who may not trust TinyURLs, as they can’t see the link’s true destination, you can send them a Preview TinyURL instead:

http://preview.tinyurl.com/27ghfn

This will take the reader to a page showing the full URL along with a clickable link to that page.

Those are the three methods I’m most familiar with for encoding long URLs in e-mails, but I’m sure there are probably more. If you have a different solution, please share!