[PM-40488] fix: clear clipboard setting does not clear the clipboard on Android 13+

app/src/main/kotlin/com/x8bit/bitwarden/data/platform/manager/clipboard/ClearClipboardWorker.kt

@@ -1,11 +1,16 @@
 package com.x8bit.bitwarden.data.platform.manager.clipboard
 
+import android.content.ClipData
+import android.content.ClipDescription
 import android.content.ClipboardManager
 import android.content.Context
 import android.content.Context.CLIPBOARD_SERVICE
+import android.os.Build
+import androidx.core.os.persistableBundleOf
 import androidx.work.Worker
 import androidx.work.WorkerParameters
 import com.bitwarden.annotation.OmitFromCoverage
+import com.bitwarden.core.util.isBuildVersionAtLeast
 
 /**
  * A worker to clear the clipboard manager.
@@ -20,7 +25,22 @@ class ClearClipboardWorker(
         appContext.getSystemService(CLIPBOARD_SERVICE) as ClipboardManager
 
     override fun doWork(): Result {
-        clipboardManager.clearPrimaryClip()
+        clipboardManager.setPrimaryClip(
+            ClipData
+                .newPlainText("", "")
+                .apply {
+                    description.extras = persistableBundleOf(
+                        if (isBuildVersionAtLeast(version = Build.VERSION_CODES.TIRAMISU)) {
+                            ClipDescription.EXTRA_IS_SENSITIVE to true
+                        } else {
+                            "android.content.extra.IS_SENSITIVE" to true
+                        },
+                    )
+                },
+        )
+        if (isBuildVersionAtLeast(version = Build.VERSION_CODES.P)) {
+            clipboardManager.clearPrimaryClip()
+        }
         return Result.success()
     }
 }

app/src/test/kotlin/com/x8bit/bitwarden/data/platform/manager/clipboard/ClearClipboardWorkerTest.kt

@@ -0,0 +1,99 @@
+package com.x8bit.bitwarden.data.platform.manager.clipboard
+
+import android.content.ClipData
+import android.content.ClipDescription
+import android.content.ClipboardManager
+import android.content.Context
+import android.os.Build
+import androidx.work.ListenableWorker
+import com.bitwarden.ui.platform.base.BaseRobolectricTest
+import io.mockk.mockk
+import org.junit.Assert.assertEquals
+import org.junit.Assert.assertFalse
+import org.junit.Assert.assertTrue
+import org.junit.Before
+import org.junit.Test
+import org.robolectric.RuntimeEnvironment
+import org.robolectric.annotation.Config
+
+class ClearClipboardWorkerTest : BaseRobolectricTest() {
+
+    private lateinit var clipboardManager: ClipboardManager
+    private lateinit var worker: ClearClipboardWorker
+
+    @Before
+    fun setup() {
+        val context = RuntimeEnvironment.getApplication()
+        clipboardManager = context.getSystemService(Context.CLIPBOARD_SERVICE) as ClipboardManager
+        worker = ClearClipboardWorker(
+            appContext = context,
+            workerParams = mockk(relaxed = true),
+        )
+    }
+
+    @Test
+    fun `doWork should clear a populated clipboard and return success`() {
+        clipboardManager.setPrimaryClip(ClipData.newPlainText("", "password"))
+
+        val result = worker.doWork()
+
+        assertTrue(clipboardManager.primaryClip?.getItemAt(0)?.text.isNullOrEmpty())
+        assertEquals(ListenableWorker.Result.success(), result)
+    }
+
+    @Test
+    fun `doWork should return success when the clipboard is already empty`() {
+        clipboardManager.clearPrimaryClip()
+
+        val result = worker.doWork()
+
+        assertFalse(clipboardManager.hasPrimaryClip())
+        assertEquals(ListenableWorker.Result.success(), result)
+    }
+
+    @Config(sdk = [Build.VERSION_CODES.TIRAMISU])
+    @Test
+    fun `doWork should overwrite the clipboard with sensitive empty content before clearing`() {
+        val overwrittenClip = captureEmptyClipboardOverwrite()
+
+        assertTrue(
+            overwrittenClip
+                ?.description
+                ?.extras
+                ?.getBoolean(ClipDescription.EXTRA_IS_SENSITIVE) == true,
+        )
+    }
+
+    @Config(sdk = [Build.VERSION_CODES.S_V2])
+    @Test
+    fun `doWork should use the legacy sensitive extra before Android 13`() {
+        val overwrittenClip = captureEmptyClipboardOverwrite()
+
+        assertTrue(
+            overwrittenClip
+                ?.description
+                ?.extras
+                ?.getBoolean("android.content.extra.IS_SENSITIVE") == true,
+        )
+    }
+
+    private fun captureEmptyClipboardOverwrite(): ClipData? {
+        var overwrittenClip: ClipData? = null
+        val listener = ClipboardManager.OnPrimaryClipChangedListener {
+            val currentClip = clipboardManager.primaryClip
+            if (
+                overwrittenClip == null &&
+                currentClip?.getItemAt(0)?.text.isNullOrEmpty()
+            ) {
+                overwrittenClip = currentClip
+            }
+        }
+        clipboardManager.setPrimaryClip(ClipData.newPlainText("", "password"))
+        clipboardManager.addPrimaryClipChangedListener(listener)
+
+        worker.doWork()
+
+        clipboardManager.removePrimaryClipChangedListener(listener)
+        return overwrittenClip
+    }
+}