Can't figure this one out, and running the Windows search troubleshooter found no issues.

Network share \\server\share\archive has a folder hierarchy like so:

2014
2015
2016

Inside each folder is more folders, say 0001, 0002, 0003, 0004 etc.

Inside those folders are files, and here's two examples:
0001_2016-02-12 XXX 01 Thing.pdf
0009_2015-12-31 XXX 02 2016 Something.pdf

If I open Windows Explorer, go to the path \\server\share\archive, and search for "2016-02-12" in the search box in the upper right, guess which file shows up.

If you answered "0001_2016-02-12 XXX 01 Thing.pdf", you guessed incorrectly. Instead only "0009_2015-12-31 XXX 02 2016 Something.pdf" shows up.

Now if I search for "_2016-02-12", both the above named files show in the search results.

So, umm, how do I get search to work properly here?

You are of course expecting Windows to work as well as Apple in this regard. As with many things, Apple implemented this right, and Windows did not. I have had similar maddening issues with the search feature of Windows and never found a proper work around. Don't know why it sucks so bad in this regard, you'd think they'd have gotten it right by now.

If you're just looking for filenames instead of file contents, I'd say just use the DOS DIR command in this case.

dir \\server\share\archive\*2016-02-12*.pdf /s

Yep, I expect personal computers to act as such and compute search results

Thanks to your suggestion Tony, I did find that typing *2016-02-12* into the Explorer search box did what I wanted. It still amusingly returns both files though.

I'm going to skip the DOS suggestion though due to Explorer providing some options I'd need to run on these files via the context menu.

As a followup, tried the same on the C:\ drive on the Windows 7 machine to make sure it wasn't a network issue (eliminating any sort of DFS, non MS server or other possible issue). Same results.

Also tried on Windows 10. Works fine there, so it looks like this search bug was fixed at some point, but not backported to Windows 7.

I use FileSearchEX because of things like this...

A lot of people resort to third party search tools on Windows. Which speaks volumes about how badly the feature got implemented in the OS. Blech.

I'm also in the camp who resorts to third party search tools. Windows search has always been terrible in every aspect, especially UI. Remember that obnoxious dog?

My personal favorite application is Everything Search. It's lightweight and super fast. I can't remember whether it can search file contents though.

Anyway, bravo, Microsoft, for pushing me further into the cloud and making your operating system more irrelevant. Searching Google Drive is a dream compared to Windows.