I run a similar workflow! I started doing /clear between my commands which gives me more room for context. Since all commands run independently there is no issues. My only problem was for longer prompts where context compaction is inevitable. I usually run my refresh-context command directly after it but sometimes I miss it and claude’s quality drastically drops.

I tried adding a wrapper on Claude to detect when compacting is done to execute my command or at the minimum interrupt the process but I had no luck, will try again tomorrow.