Updated June 15th, 2019.
You know about Recent Items, under the Apple menu, yes? It tracks Applications, Documents, and Servers– typically, and by default, it tracks the most recent ten of each. When you’re looking for a recently-used app, document, or server, the Recent Items menu can be a big time-saver. But, since it only remembers the last ten apps, the last ten documents, and the last ten servers, there’s a fair chance that the stuff you’re looking for isn’t in the Recent Items list. What a drag if the thing you want was number eleven! We need Recent Items to remember more items. Turns out all you have to do is ask.
Recent Items can remember as many as 50 apps, 50 documents, and 50 servers. Just go to System Preferences, then General. Find Recent Items toward the bottom of the General preferences and change it as you’d like. Here, I’ve set it to 30, a good middle ground.
More items means more chances that the desired app, document, or server will be in the list. Give it a try and see.
Note: the Mac’s Recent Items tracking is different and separate from the Recent Documents feature of Word, Excel, and so on. Often, the Mac’s Recent Items is better.