Landing Gear Issue, 1967 T337B

[OhioSkymaster]

When I placed the gear handle in the Retract position the gear retracted as far as I could see, but the amber "gear up" light did not illuminate and the gear handle stayed in the up position. When I manually moved the gear handle to the neutral position the amber light came on. When I extended the gear, the gear handle worked as it should and went back to neutral, and the green "gear down" light illuminated. I tried retracting the gear again and this time the amber light and gear handle worked as it should. Has anyone else experienced this? Thoughts?