diff --git a/apps/server/src/storageCleanup.test.ts b/apps/server/src/storageCleanup.test.ts
index 5f945abd1858c..c1293e3306463 100644
--- a/apps/server/src/storageCleanup.test.ts
+++ b/apps/server/src/storageCleanup.test.ts
@@ -461,6 +461,22 @@ const cleanupFixture = (
       setOpenSessionCwd: (cwd: string | null) => {
         openSessionCwd = cwd;
       },
+      openTerminal: (paths: { cwd: string; worktreePath: string | null }) =>
+        terminalListener?.({
+          type: "upsert",
+          terminal: {
+            threadId: "thread-1",
+            terminalId: "terminal-1",
+            status: "running",
+            pid: 1,
+            exitCode: null,
+            exitSignal: null,
+            hasRunningSubprocess: false,
+            label: "Terminal",
+            updatedAt: "2026-06-10T12:00:00.000Z",
+            ...paths,
+          },
+        }) ?? Effect.void,
       fullStatusCalls: () => fullStatusCalls,
       snapshotReads: () => snapshotReads,
       activate: (domainEvents: Stream.Stream<OrchestrationV2DomainEvent>) => {
@@ -1594,6 +1610,54 @@ describe("orphan worktree reports", () => {
         }),
       ),
   );
+
+  it.live.each([
+    ["win32", "cwd"],
+    ["win32", "worktreePath"],
+    ["linux", "cwd"],
+    ["linux", "worktreePath"],
+  ] as const)(
+    "matches a terminal at the worktree root with host casing rules (%s, %s)",
+    ([platform, field]) =>
+      runCleanupTest(
+        Effect.gen(function* () {
+          const fixture = yield* cleanupFixture().pipe(
+            Effect.provideService(HostProcess.Platform, platform),
+          );
+          const upper = fixture.worktree.toUpperCase();
+          yield* fixture.openTerminal(
+            field === "cwd"
+              ? { cwd: upper, worktreePath: null }
+              : { cwd: fixture.repo, worktreePath: upper },
+          );
+          const report = yield* fixture.service.runNow;
+          expect(report.entries[0]).toMatchObject(
+            platform === "win32"
+              ? { outcome: "kept", reason: "Open terminal" }
+              : { outcome: "removed" },
+          );
+        }),
+      ),
+  );
+
+  it.live.each(["win32", "linux"] as const)(
+    "matches a provider session at the worktree root with host casing rules (%s)",
+    (platform) =>
+      runCleanupTest(
+        Effect.gen(function* () {
+          const fixture = yield* cleanupFixture().pipe(
+            Effect.provideService(HostProcess.Platform, platform),
+          );
+          fixture.setOpenSessionCwd(fixture.worktree.toUpperCase());
+          const report = yield* fixture.service.runNow;
+          expect(report.entries[0]).toMatchObject(
+            platform === "win32"
+              ? { outcome: "kept", reason: "Provider session is still open" }
+              : { outcome: "removed" },
+          );
+        }),
+      ),
+  );
 });
 
 describe("storage cleanup reports and local file policies", () => {
diff --git a/apps/server/src/storageCleanup.ts b/apps/server/src/storageCleanup.ts
index 48154835e7bb4..b9f1e1f839528 100644
--- a/apps/server/src/storageCleanup.ts
+++ b/apps/server/src/storageCleanup.ts
@@ -248,8 +248,8 @@ const make = Effect.gen(function* () {
         const cwd = path.resolve(terminal.cwd);
         return (
           (terminal.worktreePath !== null &&
-            path.resolve(terminal.worktreePath) === worktreePath) ||
-          cwd === worktreePath ||
+            pathKey(terminal.worktreePath) === pathKey(worktreePath)) ||
+          pathKey(cwd) === pathKey(worktreePath) ||
           inside(worktreePath, cwd)
         );
       });
@@ -987,7 +987,7 @@ const make = Effect.gen(function* () {
           for (const session of sessions) {
             const cwd = path.resolve(session.cwd);
             if (
-              (cwd === worktreePath || inside(worktreePath, cwd)) &&
+              (pathKey(cwd) === pathKey(worktreePath) || inside(worktreePath, cwd)) &&
               (yield* providerSessions.isLive(session.id))
             )
               return waitForStop("provider session is still open");