That's difficult to predict, and it depends on what Trump's affinity for Putin is.
If Putin has tapes of Trump pissing on Russian prostitutes, and whatever is in the Epstein files, then Trump might never dare cross him, for fear that Putin would release the blackmail.
HOWEVER, Congress can override Trump. So far they have chosen not to. Still, there is heavy pressure from the US Military Industrial complex to sell more weapons to Ukraine. Raytheon (Tomahawk Missiles) and Lockheed Martin (JASSMs) are putting pressure on Congress to in turn pressure Trump to sell these weapons to Ukraine. Trump succeeded in making sure that the US won't pay for this -- the EU will pay for it (likely with frozen Russian assets). That means this is a huge win-win for the US, and there's no reason not to do it (Putin has proven his red lines are meaningless when crossed).
So, when will we see Trump sell more weapons to Ukraine? I think within 6 months will see Trump take concrete action, but it won't be Trump himself. It will be Congress passing supermajority legislation, so that Trump can say to Putin "it's out of my hands, sorry". So, if we allow a few months for legislation, I think by next summer we will see either JASSMs or Tomahawks sold to Ukraine.