Open Radar

 
Summary:
Mail will let you use boolean terms (AND, OR, NOT) in the main search bar in the upper right corner, but if you attempt to save this search as a Smart Mailbox, the Smart Mailbox does not seem to search in the same way, and the search fails.

Steps to Reproduce:
1. Open Apple Mail
2. Type a simple boolean search in the upper right-hand search bar, such as "Lucas OR Kasdan OR Brackett". This produces search results as expected.
3. Click the "Save" button in the search filter bar. The search gets translated as [Entire message][contains][Lucas OR Kasdan OR Brackett].
4. Save the Smart Mailbox as-is, without any changes, by clicking "OK".
5. Click on the title of the new Smart Mailbox to reveal its contents.

Expected Results:
That the saved search, in Smart Mailbox form, would give the same search results as received from the search bar.

Actual Results:
The Smart Mailbox does not seem to obey the same boolean commands as the search bar, and the search fails.

Version:
Mail Version 7.2 (1874)
OS X Version 10.9.2 (13C64)

Notes:
The only known workaround is to do the search as a Spotlight search (as shown in the 4th attached screenshot), instead of a Smart Mailbox. Spotlight even gives easy access to complex boolean operations in GUI form, by option-clicking the + button. However, this workaround is clumsy at best, as it does not integrate into the Mail interface.

Configuration:
Occurs in all known versions of Mavericks on multiple machines.