Acted as Mr. Walter Roch's private secretary in the Pembrokeshire bye-election of 1908, and took an active part. In the election of January 1910 spoke many times for Sir Owen Philipps, Mr. Walter Roch, and for Mr. Sidney Robinson. Spoke once or twice at the Oxford Union. Came out very strongly in favour of "disestablishment" although a keen churchman and an ardent member of a church settlement in East London. Spoke on this question at Llanelly, Llandilo, Llandovery, Lampeter, Aberaynon, Brecon, Penhiwceiber and Abercwmboi. His name was prominently mentioned at the time of the bye-election in East Carmarthenshire. He was asked to stand by four different liberal associations, but none of these invitations were accepted. Two were declined on the ground that the constituences were far from Wales, and one of the others on the ground that there would have been no conservative candidate but only a labour candidate in the field. Mr. Philipps's style of address was usually fiery, and he enjoyed being heckled.

Roland Philipps was to quote Baden Powell's words, "fanatic for scout ideals", but his interest in the scout movement, great as it was, did not prevent him from taking an active part in politics. He was eager to get into Parliament and made his political debut by offering himself a liberal candidate for East Carmarthen. As an ardent advocate for Irish home rule and Welsh disestablishment, he had the support of Mr. Lloyd George, the leader of the left wing of the Liberal Party. He failed, however, to secure nomination, owing to a Welsh-speaking candidate being preferred. In one of his speeches, he expressed his sympathy with social reform and stated that he would no longer live in the West End of London with friends of his own social class. He had taken up his abode among the poor of Bethnal Green, and meant to stick to it, as he found it a "much more cherry place."

Though he failed to secure nomination as liberal candidate for East Carmarthenshire, he was adopted in 1912, by a large majority, as candidate for South Glamorgan. His genial personality and charm of manner made him popular with all classes. Had he lived, he would probably had secured election, for he had a wonderful way of reconciling socialism to liberalism and persuading his audiences that, though their methods might be different, there was no great difference in their aims. Meanwhile, his social work in the East End of London took a more distinctively religious aspect, for we found him addressing large audiences on Mission Work, in which he emphasised the need of sympathy with our fellow men and condemned the spirit of criticism.