I feel like I am missing something incredibly simple.
Setup a VSTS project.
Created "Test Plan 002" added two configurations to it. "Windows 10, Chrome" and "Windows 10, IE". This is currently an entirely manual plan being interacted with in the browser.
Set the Kanban board to "Manual tests - Test plans -> Select a test plan -> Test Plan 002"
Created an item on the board and added some test using the option on the board card.
Tests show up on the card as expected. Tests appear in "Test Plan 002" under a requirements based suite as expected. They also display in the requirements based suite twice, because of the two configurations, as expected.
If, in the test plan I mark the first test with the "Windows 10, Chrome" configuration as "Failed" this is reflected on the kanban board card which now shows a "failed" test 1. As expected.
If, on the card in the kanban board, I right click the first test and mark it as "Failed" the corresponding test in the test plan is marked "Failed" but ONLY the one for the "windows 10, Chrome" configuration. (Why not the same test with the "Windows 10, IE" configuration?)
If, in the test plan, I right click the first test (the one with the "Windows 10, IE" config) and mark it as "Failed" nothing on the kanban board card shows as failed.
The Kanban board seems to ignore the result for, and not interact with, any test case that isn't the ones with the "Windows 10, Chrome" configuration.
I am sure I have missed a setting, but I sure can't figure out which one. Any assistance would be greatly appreciated.