Hydride shift and Ring Expansion
Ring expansion takes place in the step $\ce{D-&gt;E}$.
You were going right till the intermediate. Your intermediate will be attacked by $\ce{Br-}$ anions (as temp. is normal, therefore $\ce{S_N1}$ mechanism). Product will be B.
Then, it will form grignard reagent as C, which will react with aldehyde to produce alcohol D.
After that, it will react with HI to form a carbocation intermediate, which will rearrange to give product E.
The whole mechanism is as follows,