Is there a practical "open with" option/workaround for hyperlinks in Outlook?

My employer has a lot of proprietary software, and any time they install or upgrade commercial software they do an enormous amount of compatibility testing. As a result, we frequently use very outdated software.

One such example is Internet Explorer, which is the mandated default web browser. They do allow for Edge to be installed and used, but the default has to be IE, since all company software is known to be compatible with IE but not necessarily with Edge. So you can open Edge and then from within the program open any website you want, but if you click on a hyperlink from another application, it opens the page in IE.

This is a huge hassle, since more and more websites become incompatible with IE. In such cases, you need to click on the hyperlink, then copy the web address and paste it into Edge. So I’m wondering if there’s a way to direct the given application (generally Outlook) to open it in Edge specifically. Or some other workaround which would deal with this.

Are you on Office 365? If so, the web client has massively improved and does most of what Outlook desktop can do.

Not really. The “which app opens which kinds of files or addresses” is set by the OS at the per-user level. Outlook could in theory have its own internal setting for “open URLs with <app>” then do a bunch of extra work to follow that setting when you click a URL. But Microsoft didn’t do that.

Here’s a rough workaround that may already be what you’re doing.

In the email containing the link you want to follow, right-click and select “Copy hyperlink” If that choice isn’t available you probably right-clicked near the link, not on it. Then Alt-Tab to your Edge or Chrome or whatever browser you want to use to follow the link. Select the address bar on the browser tab you want to use, or open a new browser tab. (there are keyboard shortcuts to do this too, but they vary by browser so you’ll have to look them up yourself). Then hit paste which will copy the URL into address bar. [Enter] and you’re there.

It’s a couple more clicks and keystrokes than being able to reconfigure what your default browser is. But it may be easier than whatever workaround you’ve been doing. If a keyboard macro-ing app is one of the things installed by your employer you can probably turn that whole rigmarole into “select url, press Ctrl-Shift-E” and you’re done. If not, you’ll be stuck keystroking it every time yourself.