Email, Messaging, & Video Calls Email How to Prevent Mac OS X Mail From Breaking Links Make sure your emails arrive intact by Heinz Tschabitscher Writer A former freelance contributor who has reviewed hundreds of email programs and services since 1997. our editorial process Heinz Tschabitscher Updated on September 25, 2019 Wulf Voss / Getty Images Email Yahoo! Mail Gmail Tweet Share Email Unfortunately, the result of how macOS Mail and other programs handle plain text emails right can still be broken links. Typically, they will appear either spanning multiple lines or with a whitespace character inserted in an odd place (after a '/', for example). In both cases, the link, though clickable, will not work. Fortunately, you can take a few steps to avert this issue and send your URLs in a way that makes it easier for your recipients to see what you're sharing. These instructions apply to macOS 10.9 and later. Prevent macOS Mail From Breaking Links in Emails If links aren't working in Apple's Mail program, here are a few tips to ensure that they do. Start URLs on a line of their own. In other words, hit Return before typing or pasting the URL.If the link address is longer than 69 characters, use TinyURL or a similar service to make long URLs shorter. Mail will break any line 70 characters or longer, destroying the link for some email programs. For easy access to TinyURL, you can install a system service. The Rich Text Alternative Alternatively, you can send the email using rich formatting and turn any text into a link. Here's how to turn this feature on and use it to add links to an email. Use rich text only if you know the recipient reads the HTML version, though. While Mac OS X Mail includes a plain text alternative with the email, it will lack the link. In Mail, open the Preferences by selecting it under the File menu or pressing Command+comma ( , ). Click the Composing tab. Under the Message Format menu, select Rich Text. To insert a rich-text link into an email, start composing a message and highlight the words you want to add the link to. Select Add Link under the Edit menu. The keyboard shortcut to add a link is Command+K. Type (or paste) the address of the site you want to link to and click OK. The text you highlighted will become a link to the URL you entered. It will turn blue and gain an underline. Finish your message and send it as usual.