Distillation

🔴 (03:46) User stated package managers always need network access to fetch and install packages; offline upgrade mode is supported only for curl-installed binaries.
🔴 (03:46) User stated nightly builds are GitHub-only, so nightly version existence checks always use the curl/GitHub lookup regardless of the current installation method.
🔴 (03:46) User stated trailing path separators should be stripped for path comparison, but never from a bare root such as /; for example, ~/.local/bin/ must compare equal to ~/.local/bin. Implementation is in packages/cli/src/lib/binary.ts via stripTrailingSep(p: string).
🔴 (03:46) User stated a caller receives the successful probe response so it never repeats the successful probe request.
🔴 (03:46) User stated sentry cli upgrade nightly means “Switch to nightly channel and update.”
🔴 (03:46) User supplied a change in packages/cli/src/commands/cli/upgrade.ts where validateMethod() normalizes a non-channel versionArg with VERSION_PREFIX_REGEX; Homebrew rejects a specifically pinned version unless isNightlyVersion(pinnedVersion) is true.
🔴 (03:46) User supplied a change in packages/cli/src/commands/cli/upgrade.ts where target resolution returns { kind: "target", target: resolvedTarget, source }, preserving an UpgradeSource alongside the resolved target.

Observations