In 1908 Drummond and Helen Craggs were campaigning successfully against Churchill again. That year, Flora also became a paid organiser at the WSPU headquarters and hired a boat so that she could approach the Palace of Westminster from the River Thames to harangue the members of parliament sitting on the riverside terrace. When Mary Phillips, who had worked in Glasgow WSPU, was released from prison after serving the longest (3 month) sentence she was welcomed by Flora Drummond, with bagpipes and other suffragettes who posed in tartan  for a picture under the slogan "Ye Mauna Tramp on the Scotch Thistle Laddie". The Scottish suffragettes present compared their struggle to the campaign of William Wallace. Drummond also welcomed Catherine Corbett and others released from hunger strike at Dundee Gaol after riot at Winston Churchill's meeting in Dundee. Flora Drummond was a key organiser of the Trafalgar Square rally in October 1908 which led to a three-month term in Holloway along with Christabel and Emmeline Pankhurst for "incitement to rush the House of Commons". The women had been given the option of being bound over to keep the peace for twelve months instead of a custodial sentence but all three opted for Holloway. Flora was in the first trimester of pregnancy when she was imprisoned and after fainting and being taken to the hospital wing she was granted early release on the grounds of ill-health. As Drummond was leaving the prison Emmeline Pankhurst broke the "silence rule" which forbade the suffragette prisoners from speaking to each other and called out 'I "am" glad because now you will be able to carry on the work'. Drummond had been given a Hunger Strike Medal 'for Valour' by WSPU, after 9 imprisonments and a number of hunger strikes. In October 1909, Drummond was the organiser of the first militant procession in Edinburgh as a response to a critical comment from the WSPU leadership in their newsletter "Votes for Women" which said 'Beautiful, haughty, dignified, stern Edinburgh, with your cautious steadfast people, you have not yet woken up to take part in our militant methods.' The theme of the march was 'have done and can do and will do' and featured women carrying banners and playing bagpipes dressed either in their working clothes or as female historical Scottish figures. Tens of thousands turned out on to the streets of Edinburgh to watch the parade and the event was considered by the "Edinburgh Evening Dispatch" to have been a success.