We investigate the interaction between compactness principles and guessing principles in the Radin forcing extensions. In particular, we show that in any Radin forcing extension with respect to a measure sequence on κ, if κ is weakly compact, then ♢(κ) holds. This provides contrast with a well-known theorem of Woodin, who showed that in a certain Radin extension over a suitably prepared ground model relative to the existence of large cardinals, the diamond principle fails at a strongly inaccessible Mahlo cardinal. Refining the analysis of the Radin extensions, we consistently demonstrate a scenario where a compactness principle, stronger than the diagonal stationary reflection principle, holds yet the diamond principle fails at a strongly inaccessible cardinal, improving a result from [O. B. -Neria, Diamonds, compactness, and measure sequences, J. Math. Log. 19(1) (2019) 1950002].