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The HTTP tool returned `ApprovalRequirement::Always` for requests with credentials, but `Always` is hardcoded to ignore the session auto-approve set. This meant users who clicked "always" were re-prompted on every subsequent HTTP call — the UI offered "always" but the backend ignored it. Two fixes: 1. HTTP credentialed requests now return `UnlessAutoApproved` instead of `Always`, so the session auto-approve set is respected. 2. `StatusUpdate::ApprovalNeeded` now carries `allow_always: bool`. All channel UIs (Telegram, Slack, Signal, REPL, Web) conditionally hide the "always" option when a tool truly requires per-invocation approval (`ApprovalRequirement::Always`, e.g. destructive shell commands). Also boxes `PendingApproval` in `AgenticLoopResult::NeedApproval` to fix a pre-existing clippy `large_enum_variant` warning. Regression tests included (test_credentialed_requests_respect_auto_approve, test_allow_always_matches_approval_requirement) but CI heuristic cannot detect them in cross-fork PR diffs. [skip-regression-check] Co-authored-by: Tyler <[email protected]>