diff --git a/src/tmux-manager.ts b/src/tmux-manager.ts
index 9fdd2bda..6fc9dcd6 100644
--- a/src/tmux-manager.ts
+++ b/src/tmux-manager.ts
@@ -770,11 +770,27 @@ export function buildRemoteLaunchCommand(options: {
   // `defaultRemoteCommandForMode`: `claude` lives under a per-user PATH entry that
   // only an interactive login shell resolves (see that function's comment).
   const override = remote.commands?.[mode];
-  const modeCommand = override
-    ? override
-    : mode === 'claude'
-      ? remoteLoginShellCommand(`claude${buildClaudePermissionFlags(claudeMode, allowedTools)}`)
-      : defaultRemoteCommandForMode(mode);
+  let modeCommand: string;
+  if (override) {
+    modeCommand = override;
+  } else if (mode === 'claude') {
+    // Deterministic conversation pinning for SSH-remote claude (mirrors the
+    // docker-claude shape in claudeDockerPaneCommand): the FIRST run creates
+    // the conversation under --session-id <sessionId>; a respawn / reattach
+    // re-runs the same idempotent command, --session-id exits non-zero
+    // ("already in use"), and the `||` fallback RESUMES that same
+    // conversation. Without a pinned id, every reattach relaunched a bare
+    // `claude` and started a NEW conversation (found live 2026-08-29: remote
+    // claude ctrl-d / ctrl-c relaunched a fresh session). A per-host
+    // `commands.claude` override stays authoritative (admin's explicit
+    // choice) and skips this entirely.
+    const permFlags = buildClaudePermissionFlags(claudeMode, allowedTools);
+    modeCommand = remoteLoginShellCommand(
+      `claude${permFlags} --session-id ${sessionId} || claude${permFlags} --resume ${sessionId}`
+    );
+  } else {
+    modeCommand = defaultRemoteCommandForMode(mode);
+  }
   const remoteName = remoteTmuxSessionName(sessionId);
 
   // Innermost: the command tmux runs in the new pane. Run via `/bin/sh -c` by
diff --git a/src/utils/omp-session-resolver.ts b/src/utils/omp-session-resolver.ts
index e01ac00a..b3959b76 100644
--- a/src/utils/omp-session-resolver.ts
+++ b/src/utils/omp-session-resolver.ts
@@ -22,6 +22,23 @@ import { join, sep } from 'node:path';
 /** A real OMP session file is `<ISO-ish-timestamp>_<uuid>.jsonl`; only the uuid matters here. */
 const OMP_SESSION_FILE_PATTERN = /^.+_([a-zA-Z0-9-]+)\.jsonl$/;
 
+/**
+ * Strip a trailing `/` from a workingDir unless it is the root itself.
+ *
+ * Case paths routinely end in `/` — a remote case's `remotePath` is stored
+ * verbatim (e.g. `/home/user/dotfiles/`) — but omp persists sessions under
+ * the slash-less mangle (`-dotfiles`) with a header `cwd` of
+ * `/home/user/dotfiles`. Without normalization, the trailing slash survives
+ * the mangle (`-dotfiles-`), `readdirSync` returns null for a directory that
+ * exists, and OMP respawn pinning silently degrades to the ambiguous
+ * `--continue` (found live 2026-08-29: a remote OMP ctrl-c relaunched a fresh
+ * conversation instead of resuming). Exported so the same normalization is
+ * used for the header-`cwd` comparison in {@link resolveAndClaimOmpSessionId}.
+ */
+export function stripTrailingSlash(workingDir: string): string {
+  return workingDir.length > 1 && workingDir.endsWith('/') ? workingDir.slice(0, -1) : workingDir;
+}
+
 /**
  * Mirrors `omp`'s own directory mangling. Confirmed empirically against real
  * `~/.omp/agent/sessions/` directory names (2026-08-27): unlike Claude Code's
@@ -45,8 +62,9 @@ export function mangleOmpWorkingDir(workingDir: string): string {
   // omp's actual behavior on a symlinked-home setup; guessing wrong here would
   // trade one silent mismatch for a different one.
   const home = homedir();
+  const normalized = stripTrailingSlash(workingDir);
   const relative =
-    workingDir === home || workingDir.startsWith(home + sep) ? workingDir.slice(home.length) : workingDir;
+    normalized === home || normalized.startsWith(home + sep) ? normalized.slice(home.length) : normalized;
   return relative.replace(/\//g, '-');
 }
 
@@ -183,7 +201,9 @@ export function resolveAndClaimOmpSessionId(workingDir: string): string | null {
     }
     if (mtimeMs <= newestMtime) continue;
     const header = readOmpSessionHeader(filePath);
-    if (!header || header.cwd !== workingDir || claimedOmpSessionIds.has(header.id)) continue;
+    // Compare against the slash-normalized workingDir: the session's own
+    // workingDir may carry a trailing slash while omp's header cwd never does.
+    if (!header || header.cwd !== stripTrailingSlash(workingDir) || claimedOmpSessionIds.has(header.id)) continue;
     newestMtime = mtimeMs;
     newestId = header.id;
   }
diff --git a/test/omp-session-resolver.test.ts b/test/omp-session-resolver.test.ts
index ed6d2f60..d1d528b8 100644
--- a/test/omp-session-resolver.test.ts
+++ b/test/omp-session-resolver.test.ts
@@ -41,6 +41,15 @@ describe('mangleOmpWorkingDir', () => {
     const sibling = `${homedir()}-other/dev/foo`;
     expect(mangleOmpWorkingDir(sibling)).toBe(sibling.replace(/\//g, '-'));
   });
+
+  it('normalizes a trailing slash so a remote case path resolves to the same dir', () => {
+    // Regression (2026-08-29): remote case paths are stored verbatim with a
+    // trailing slash (e.g. `/home/user/dotfiles/`), but omp persists sessions
+    // under the slash-less mangle (`-dotfiles`). Before the fix this produced
+    // `-dotfiles-`, readdirSync returned null for an existing dir, and OMP
+    // respawn pinning silently degraded to the ambiguous `--continue`.
+    expect(mangleOmpWorkingDir(join(homedir(), 'dotfiles') + '/')).toBe('-dotfiles');
+  });
 });
 
 describe('findLatestOmpSessionId', () => {
diff --git a/test/tmux-manager.test.ts b/test/tmux-manager.test.ts
index 4c87f96e..27cea00d 100644
--- a/test/tmux-manager.test.ts
+++ b/test/tmux-manager.test.ts
@@ -172,6 +172,21 @@ describe('TmuxManager (unit)', () => {
       expect(command).toContain('exec "${SHELL:-/bin/sh}" -i -l -c');
       expect(command).toContain('claude --dangerously-skip-permissions');
     });
+
+    it('pins SSH-remote claude to the Codeman session id so a respawn resumes the same conversation', () => {
+      // Regression (2026-08-29): remote claude was launched as a bare `claude …`,
+      // so every reattach/respawn after a pane death (user ctrl-d or ctrl-c exit)
+      // started a NEW conversation. The launch now mirrors the docker-claude shape:
+      // `--session-id <id>` to create, with a `|| --resume <id>` fallback so the
+      // idempotent re-run resumes instead of erroring ("already in use").
+      const command = buildRemoteLaunchCommand({
+        mode: 'claude',
+        remote: { hostId: 'gpu-box', label: 'GPU Box', host: '10.0.0.42', username: 'ubuntu', remotePath: '/w' },
+        sessionId: 'abc123def456',
+      });
+      expect(command).toContain('claude --dangerously-skip-permissions --session-id abc123def456');
+      expect(command).toContain('claude --dangerously-skip-permissions --resume abc123def456');
+    });
   });
 
   describe('remote kill command builder', () => {