Reproduction steps:
1. Open the attached “repro_IN-85766“ project
2. In the Scene view overlay, expand the “Debug Draw Mode“ dropdown
3. Select “Custom → My Draw Mode“
4. Go out of the dropdown
5. In the Scene view overlay, press the “Debug Draw Mode“ button
6. Press the “Debug Draw Mode“ button again
7. Observe the Console

Expected result: No error is thrown and the "My Draw Mode" option is active again in the “Debug Draw Mode“ dropdown
Actual result: The “InvalidOperationException: Sequence contains no matching element“ error is thrown and the "My Draw Mode" option is not active in the “Debug Draw Mode“ dropdown

Reproducible with: 6000.0.23f1
Couldn’t test with: 2021.3.44f1, 2022.3.50f1 - The “Debug Draw Mode“ button doesn’t exist, there’s only the dropdown button, making it impossible to test this issue

Reproducible on: Windows 10 (22H2), Windows 11 (10.0.22631) (user’s)
Not reproducible on: No other environments tested