You guessed right, I did insert it properly and felt the rumble. I believe that provided you put the correct inserts in the pipe for the pipe manufacturer you can then put a different manufacturers fitting on as all the pipes have the same outside diameter. Because the original was a Hepworth pipe I put a Hep2O fitting on but lost confidence when it leaked hence the change to Speedfit which I have always liked and I also like the added security of tightening them after insertion.OP you now say you have put a new hep insert and a speedfit reducer, you have made your situation worse by mixing manufacturers.
The hep fittings/inserts have the "rumble strip" which allows you to feel that the fitting is fully inserted. I suspect you had not fully inserted the fitting the first time, it is actually quite a firm pressure required to do so, a little smear of silicone grease aids insertion and lubricates the o-ring making dismantling easier if needed. I know you'll say you did it properly, but I bet you didn't!