diff --git a/Sources/ShotdeckCore/Support/TransportSettings.swift b/Sources/ShotdeckCore/Support/TransportSettings.swift
index cf907f1..c278d61 100644
--- a/Sources/ShotdeckCore/Support/TransportSettings.swift
+++ b/Sources/ShotdeckCore/Support/TransportSettings.swift
@@ -189,16 +189,33 @@ public enum OneDriveLocator {
         fileManager: FileManager = .default
     ) -> Bool {
         let probeURL = folder.appendingPathComponent(".redline-probe-\(UUID().uuidString)")
+        // Belt-and-suspenders cleanup, unconditional: AtomicFile.write renames the temp
+        // file onto probeURL and THEN fsyncs the containing directory — if that last
+        // fsync throws, the probe file already exists on disk but the catch below
+        // returns false before ever reaching the explicit removeItem call. And if the
+        // explicit removeItem itself throws, this is the only retry it gets. Either
+        // way, never leave the probe file behind just because we're about to return.
+        defer {
+            if fileManager.fileExists(atPath: probeURL.path) {
+                try? fileManager.removeItem(at: probeURL)
+            }
+        }
+
         do {
             try AtomicFile.write(Data(), to: probeURL)
         } catch {
             return false
         }
+
         do {
             try fileManager.removeItem(at: probeURL)
         } catch {
             return false
         }
-        return true
+
+        // Only true when the explicit removal above actually succeeded AND the file is
+        // confirmed gone — never trust a removeItem call that returned without throwing
+        // as proof of anything on a File Provider domain.
+        return !fileManager.fileExists(atPath: probeURL.path)
     }
 }
diff --git a/Tests/ShotdeckCoreTests/TransportSettingsTests.swift b/Tests/ShotdeckCoreTests/TransportSettingsTests.swift
index 835cfef..3eb787f 100644
--- a/Tests/ShotdeckCoreTests/TransportSettingsTests.swift
+++ b/Tests/ShotdeckCoreTests/TransportSettingsTests.swift
@@ -160,6 +160,49 @@ func probeWritableFalseForAPlainFilePath() throws {
     #expect(!OneDriveLocator.probeWritable(at: filePath))
 }
 
+/// The write itself succeeds (a real probe file lands on disk via AtomicFile.write,
+/// which never touches this injected FileManager — it uses raw POSIX calls), but the
+/// FIRST call to `removeItem(at:)` throws, simulating a transient File Provider
+/// removal failure. probeWritable's own defer-based cleanup must retry and succeed
+/// (the second call through this same override falls through to `super`), so no
+/// probe file is left behind even though the function correctly still reports false
+/// (the removal it explicitly attempted did fail).
+private final class ThrowOnceOnRemoveFileManager: FileManager, @unchecked Sendable {
+    private let lock = NSLock()
+    private var hasThrown = false
+
+    override func removeItem(at URL: URL) throws {
+        lock.lock()
+        let shouldThrow = !hasThrown
+        hasThrown = true
+        lock.unlock()
+        if shouldThrow {
+            throw NSError(domain: "ShotdeckCoreTests.ThrowOnceOnRemove", code: 1)
+        }
+        try super.removeItem(at: URL)
+    }
+}
+
+@Test
+func probeWritableFalseAndLeavesNoProbeFileWhenRemoveItemThrowsOnce() throws {
+    // Directory fsync failure (the OTHER way probeWritable's cleanup can be needed) has
+    // no injectable seam: AtomicFile.write's directory fsync is a raw Darwin fsync(2)
+    // call on an already-open file descriptor, not parameterized by any FileManager or
+    // other dependency this test can substitute, and there is no portable way to make
+    // fsync(2) itself fail via chmod or other standard test techniques (fsync failures
+    // are OS/filesystem/hardware-level events). Covering the removeItem-throws path
+    // (below) is what this test does; the fsync-throws path is covered by code
+    // inspection only — the same `defer` block guards both.
+    let dir = try makeTransportTemporaryDirectory(prefix: "shotdeck-probe-remove-throws")
+    defer { try? FileManager.default.removeItem(at: dir) }
+    let injectedFileManager = ThrowOnceOnRemoveFileManager()
+
+    #expect(!OneDriveLocator.probeWritable(at: dir, fileManager: injectedFileManager))
+
+    let leftovers = try FileManager.default.contentsOfDirectory(atPath: dir.path)
+    #expect(leftovers.isEmpty)
+}
+
 struct TransportDefaultsSuite {
     let name: String
     let defaults: UserDefaults