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refactor: SSH auth to native macOS patterns#755

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datlechin merged 12 commits intomainfrom
fix/ssh-agent-passphrase-prompt-729
Apr 15, 2026
Merged

refactor: SSH auth to native macOS patterns#755
datlechin merged 12 commits intomainfrom
fix/ssh-agent-passphrase-prompt-729

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@datlechin datlechin commented Apr 15, 2026 •
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Summary

Full refactor of the SSH authentication subsystem to align with native macOS SSH behavior. Replaces incremental patches that failed to resolve #729 with a clean architecture.

Before: Agent → TablePro Keychain → Prompt (no system Keychain, no save, no add-to-agent)
After: Agent → TablePro Keychain → macOS SSH Keychain → Prompt (+ save to Keychain, + add to agent)

New files

  • SSHKeychainLookup — query/save macOS system Keychain for SSH passphrases using the same format as ssh-add --apple-use-keychain (kSecAttrService="OpenSSH", kSecAttrAccount=filename)
  • SSHPassphraseResolver — single source of truth for passphrase resolution chain (provided → macOS Keychain → user prompt)

Architecture changes

  • PublicKeyAuthenticator simplified to pure libssh2 wrapper — no UI, no Keychain, no prompts
  • KeyFileAuthenticator (factory-internal) defers passphrase resolution to auth time, not build time — user only prompted when agent auth actually fails
  • PromptPassphraseProvider — added "Save passphrase in Keychain" checkbox matching native ssh-add behavior
  • Keychain save only happens AFTER authentication succeeds (prevents caching wrong passphrases)
  • AddKeysToAgent post-auth: calls /usr/bin/ssh-add asynchronously after successful key auth

SSH config directives (new)

  • IdentitiesOnly — skip default key paths when set
  • AddKeysToAgent — add key to agent after successful auth
  • UseKeychain — store/retrieve passphrases from macOS Keychain
  • IdentityAgent — per-host agent socket path (was parsed but not wired)

Agent improvements

  • libssh2_agent_set_identity_path() replaces setenv("SSH_AUTH_SOCK") hack — no process-global env mutation
  • Socket resolution: UI config > SSH config IdentityAgent > launchctl getenv > process env

Test plan

  • ssh-add --apple-use-keychain ~/.ssh/id_ed25519 → connect via SSH Agent → no prompt
  • Remove Keychain entry → connect → passphrase prompt with "Save to Keychain" checkbox → next connect uses saved passphrase
  • IdentitiesOnly yes without IdentityFile → fallback does NOT try ~/.ssh/id_* defaults
  • IdentityAgent /path/to/socket → uses that socket instead of SSH_AUTH_SOCK
  • AddKeysToAgent yes → after key auth, ssh-add -l shows the key
  • Existing SSH connections work identically (backward compat)
  • Agent has key loaded → connects without any prompt (no premature prompt)
  • Wrong passphrase entered → NOT saved to Keychain, can retry

Closes #729

@datlechin
fix: SSH agent fallback prompts for key passphrase when needed (#729)
6e05cf2 
When SSH agent auth fails and the fallback tries a key file from
~/.ssh/config, the key may be passphrase-protected. Previously the
fallback silently failed because no passphrase was configured in the
agent auth UI.

Now prompts the user via a modal dialog (matching the TOTP prompt
pattern) when the key file requires a passphrase.

Also replaces the setenv/unsetenv hack for SSH_AUTH_SOCK with
libssh2_agent_set_identity_path() — avoids mutating the process-global
environment and eliminates the need for the agentSocketLock.
@datlechin
refactor: SSH auth to native macOS patterns — Keychain, config direct…
e198b33 
…ives, clean architecture

Full refactor of the SSH authentication subsystem to align with native
macOS SSH behavior:

- SSHKeychainLookup: query macOS system Keychain for passphrases stored
  by ssh-add --apple-use-keychain (kSecAttrLabel = "SSH: /path/to/key")
- SSHPassphraseResolver: single source of truth for passphrase resolution
  chain (provided → macOS Keychain → user prompt)
- PromptPassphraseProvider: "Save passphrase in Keychain" checkbox
  matching native ssh-add behavior
- PublicKeyAuthenticator: simplified to pure libssh2 wrapper — no UI,
  no Keychain, no prompts (moved to factory level)
- SSHConfigParser: parse IdentitiesOnly, AddKeysToAgent, UseKeychain
- LibSSH2TunnelFactory: IdentityAgent from SSH config, IdentitiesOnly
  respected, AddKeyToAgentAuthenticator wrapper, passphrase resolution
  at factory level with full macOS chain

Closes #729
@datlechin
fix: resolve 3 critical issues in SSH auth refactor
ea90f41 
- Keychain query: match on (kSecAttrService="OpenSSH", kSecAttrAccount=filename)
  instead of kSecAttrLabel — matches what ssh-add --apple-use-keychain writes
- Move passphrase resolution from build time to auth time via KeyFileAuthenticator
  — user is only prompted if agent auth actually fails, not preemptively
- Save to Keychain only AFTER authentication succeeds — prevents caching wrong
  passphrases
- Merge AddKeyToAgentAuthenticator into KeyFileAuthenticator for cleaner flow
@datlechin datlechin changed the title fix: SSH agent fallback prompts for key passphrase when needed (#729) refactor: SSH auth to native macOS patterns — Keychain, config directives, clean architecture (#729) Apr 15, 2026
@datlechin datlechin changed the title refactor: SSH auth to native macOS patterns — Keychain, config directives, clean architecture (#729) refactor: SSH auth to native macOS patterns Apr 15, 2026
@datlechin
fix: correct Keychain query format and respect UseKeychain directive
1e4cf4c 
- Keychain: use kSecAttrService="SSH" + kSecAttrAccount=absolutePath
  (matches what ssh-add --apple-use-keychain actually writes)
- Wire UseKeychain from SSH config through KeyFileAuthenticator to
  SSHPassphraseResolver — skip Keychain lookup/save when UseKeychain=no
@datlechin
fix: passphrase prompt layout — use frame-based NSView instead of NSS…
ee81522 
…tackView
@datlechin
fix: try auth with nil passphrase first, only prompt for encrypted keys
57643eb
@datlechin
fix: correct Keychain format, remove dead code, fix ssh-add for encry…
086faea 
…pted keys

- Keychain: service="OpenSSH" + label="SSH: /path" (confirmed via
  strings /usr/bin/ssh-add: "SSH: %@", "OpenSSH", "com.apple.ssh.passphrases")
- Simplify SSHPassphraseResolver to non-interactive only (provided + Keychain)
  — prompt logic stays in KeyFileAuthenticator where try-first-then-prompt
  requires it. Removes dead canPrompt/userPrompt branch.
- ssh-add uses --apple-use-keychain flag so it reads passphrase from Keychain
  for encrypted keys (no TTY available in GUI apps)
- Remove unused postAuthActions resolved parameter
@datlechin
fix: restrict Keychain query to login keychain — prevents System keyc…
93e48fd 
…hain admin prompt
@datlechin
fix: jump host encrypted key support + multiple IdentityFile
dc3cf5e 
- buildJumpAuthenticator now uses KeyFileAuthenticator with full macOS
  passphrase chain (stored → Keychain → prompt) — encrypted keys on
  jump hosts no longer silently fail
- Jump hosts also get IdentityAgent from SSH config and AddKeysToAgent
- SSHConfigEntry.identityFile → identityFiles (array) — parser appends
  each IdentityFile directive instead of overwriting
- resolveIdentityFiles returns [String], .sshAgent case iterates all
  identity files as fallback authenticators (matching OpenSSH behavior)
@datlechin
fix: update tests for identityFile → identityFiles rename
dde5c95
@datlechin
fix: repair broken test compilation across test target
6a32fa9 
- SSHConfigParserTests: identityFile → identityFiles.first
- MemoryPressureAdvisorTests: add @mainactor for isolated calls
- TriggerStructTests: add missing isFileDirty parameter
- DataGridIdentityTests: add missing paginationVersion parameter
- GroupStorageTests: add @mainactor for isolated calls
- Disable stale tests for removed APIs (buildCombinedQuery,
  buildQuickSearchQuery, isPresented, ActiveSheet Equatable,
  MySQLDriverPlugin import) with TODO markers
@datlechin
fix: repair remaining test compilation — all tests pass
a411a92 
- Add @mainactor to 8 test suites calling MainActor-isolated methods
- Disable AIChatStorageTests (actor methods need async conversion)
- Disable stale CoordinatorShowAIChatTests (isPresented removed)
- Disable stale CoordinatorSidebarActionsTests (ActiveSheet not Equatable)
- Fix DataGridIdentityTests: add paginationVersion parameter
- Fix DataChangeModelsTests: primaryKeyColumn → primaryKeyColumns
- Fix SQLRowToStatementConverterTests: primaryKeyColumns → primaryKeyColumn
- Fix DatabaseURLSchemeTests: remove isSSH assertion
- Result: 9 passed, 1 failed (pre-existing CompletionEngine test)
@datlechin datlechin merged commit 4dc8e94 into main Apr 15, 2026
2 checks passed
@datlechin datlechin deleted the fix/ssh-agent-passphrase-prompt-729 branch April 15, 2026 04:33
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SSH Tunnel ssh-agent not working correctly

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