He was involved in the Winnipeg general strike of 1919, and subsequently ran for office as a candidate of the Labour Party.
[2] Tipping was elected to the Winnipeg trades council during this period, and helped to form in the Dominion Labour Party in 1918.
After the strike was suppressed, Tipping was arrested for addressing an open-air meeting in defiance of a Winnipeg by-law.
Tipping was later sent by the Strike Committee to Ottawa, to petition the federal government for a jury trial for other strikers arrested on charges of seditious conspiracy.
In the 1920 provincial election, Tipping ran in the Winnipeg constituency as part of a "united labour" slate.