diff --git a/projectBlueWater/src/main/java/com/lasthopesoftware/bluewater/client/stored/library/items/files/external/ExternalContentRepository.kt b/projectBlueWater/src/main/java/com/lasthopesoftware/bluewater/client/stored/library/items/files/external/ExternalContentRepository.kt
index f5bdd3cb4..eda82b750 100644
--- a/projectBlueWater/src/main/java/com/lasthopesoftware/bluewater/client/stored/library/items/files/external/ExternalContentRepository.kt
+++ b/projectBlueWater/src/main/java/com/lasthopesoftware/bluewater/client/stored/library/items/files/external/ExternalContentRepository.kt
@@ -4,6 +4,7 @@ import android.content.ContentResolver
 import android.content.ContentValues
 import android.os.Build
 import android.provider.MediaStore
+import com.lasthopesoftware.bluewater.shared.lazyLogger
 import com.lasthopesoftware.promises.extensions.preparePromise
 import com.lasthopesoftware.resources.executors.ThreadPools
 import com.lasthopesoftware.resources.uri.toURI
@@ -18,6 +19,10 @@ class ExternalContentRepository(
 	private val publicDirectoryLookup: GetPublicDirectories,
 ) : HaveExternalContent {
 
+	companion object {
+		private val logger by lazyLogger<ExternalContentRepository>()
+	}
+
 	override fun promiseNewContentUri(externalContent: ExternalContent): Promise<URI?> =
 		externalContent
 			.toContentValues()
@@ -61,12 +66,15 @@ class ExternalContentRepository(
 			null,
 			null
 		)
-
-		Unit
 	}
 
 	override fun removeContent(uri: URI): Promise<Boolean> = ThreadPools.io.preparePromise {
-		val deletedRecords = contentResolver.delete(uri.toUri(), null, null)
-		deletedRecords > 0
+		try {
+			val deletedRecords = contentResolver.delete(uri.toUri(), null, null)
+			deletedRecords > 0
+		} catch (e: Throwable) {
+			logger.error("Unable to delete file at uri $uri.", e)
+			false
+		}
 	}
 }
diff --git a/projectBlueWater/src/test/java/com/lasthopesoftware/bluewater/client/stored/library/items/files/external/GivenContent/AndContentResolverThrowsException/WhenRemovingTheContent.kt b/projectBlueWater/src/test/java/com/lasthopesoftware/bluewater/client/stored/library/items/files/external/GivenContent/AndContentResolverThrowsException/WhenRemovingTheContent.kt
new file mode 100644
index 000000000..8f181e7ba
--- /dev/null
+++ b/projectBlueWater/src/test/java/com/lasthopesoftware/bluewater/client/stored/library/items/files/external/GivenContent/AndContentResolverThrowsException/WhenRemovingTheContent.kt
@@ -0,0 +1,36 @@
+package com.lasthopesoftware.bluewater.client.stored.library.items.files.external.GivenContent.AndContentResolverThrowsException
+
+import android.app.RecoverableSecurityException
+import com.lasthopesoftware.AndroidContext
+import com.lasthopesoftware.bluewater.client.stored.library.items.files.external.ExternalContentRepository
+import com.lasthopesoftware.bluewater.shared.promises.extensions.toExpiringFuture
+import io.mockk.every
+import io.mockk.mockk
+import org.assertj.core.api.Assertions.assertThat
+import org.junit.Test
+import java.net.URI
+
+class WhenRemovingTheContent : AndroidContext() {
+	companion object {
+
+		private val sut by lazy {
+			ExternalContentRepository(
+				mockk {
+					every { delete(any(), null, null) } throws RecoverableSecurityException(Exception(), "whoops", mockk())
+				},
+				mockk(),
+			)
+		}
+
+		private var isRemoved = false
+	}
+
+	override fun before() {
+		isRemoved = sut.removeContent(URI("content://stuff-here")).toExpiringFuture().get() == true
+	}
+
+	@Test
+	fun `then isRemoved is false`() {
+		assertThat(isRemoved).isFalse
+	}
+}
diff --git a/projectBlueWater/src/test/java/com/lasthopesoftware/bluewater/client/stored/library/items/files/external/GivenContent/WhenRemovingTheContent.kt b/projectBlueWater/src/test/java/com/lasthopesoftware/bluewater/client/stored/library/items/files/external/GivenContent/WhenRemovingTheContent.kt
new file mode 100644
index 000000000..e2fa2039b
--- /dev/null
+++ b/projectBlueWater/src/test/java/com/lasthopesoftware/bluewater/client/stored/library/items/files/external/GivenContent/WhenRemovingTheContent.kt
@@ -0,0 +1,35 @@
+package com.lasthopesoftware.bluewater.client.stored.library.items.files.external.GivenContent
+
+import com.lasthopesoftware.AndroidContext
+import com.lasthopesoftware.bluewater.client.stored.library.items.files.external.ExternalContentRepository
+import com.lasthopesoftware.bluewater.shared.promises.extensions.toExpiringFuture
+import io.mockk.every
+import io.mockk.mockk
+import org.assertj.core.api.Assertions.assertThat
+import org.junit.Test
+import java.net.URI
+
+class WhenRemovingTheContent : AndroidContext() {
+	companion object {
+
+		private val sut by lazy {
+			ExternalContentRepository(
+				mockk {
+					every { delete(any(), null, null) } returns 464
+				},
+				mockk(),
+			)
+		}
+
+		private var isRemoved = false
+	}
+
+	override fun before() {
+		isRemoved = sut.removeContent(URI("content://ZqUbxDqDR")).toExpiringFuture().get() == true
+	}
+
+	@Test
+	fun `then isRemoved is true`() {
+		assertThat(isRemoved).isTrue
+	}
+}