@nefarious Welcome to the forum, and thank you for your write-up!
A few comments:
Version 2026.5.0 has introduced numerous bugs in the search engine:
- The Search function is not matching search terms with matching words in the Notes field within Login-type or Notes-type vault items. · Issue #21000 · bitwarden/clients · GitHub
- Seach doesn't find inner attributes anymore · Issue #21042 · bitwarden/clients · GitHub
- Search does not find an item if the name starts with accent letter · Issue #21045 · bitwarden/clients · GitHub
- Indexed searching in custom fields does not tokenize field label or field value · Issue #21062 · bitwarden/clients · GitHub
If possible, download version 2026.4.0 of the portable Desktop app, and see if any of your problems are fixed. The portable version of the app will not affect your current installation — when first launched, it will create a subfolder named bitwarden-appdata in the same folder where you saved the Bitwarden-Portable-2026.4.0.exe file; to uninstall after you are done testing, simply delete the .exe file and its subfolder.
The Lunr search engine tokenizes using space and hyphen characters as separators. However, by default, searching in the browser extension, desktop app, and web app will insert leading and trailing wildcards for each of your search terms (although this is one function that may not be working reliably in version 2026.5.0). Thus, all of your “not found” examples should be found (in version 2026.4.0 and earlier).
In addition, normally, search terms separated by spaces are combined using boolean OR, so in your examples, the example token should have been sufficient to find both of the entries, and adding the second term (ilo, ma, etc.) should only surface additional entries, not hide the entries that you were trying to find. I have confirmed that in version 2026.5.0 of the desktop app, the search behaves as you have described, which is not the expected behavior.
I think that what you have described is a new bug, different from the ones that I listed above (although it bears some similarity to Issue #21062). Bugs should generally be reported on Github.