diff --git a/app/src/main/java/com/nextcloud/client/jobs/autoUpload/FileSystemRepository.kt b/app/src/main/java/com/nextcloud/client/jobs/autoUpload/FileSystemRepository.kt
index b322b1bc7fc4..96756a0646b8 100644
--- a/app/src/main/java/com/nextcloud/client/jobs/autoUpload/FileSystemRepository.kt
+++ b/app/src/main/java/com/nextcloud/client/jobs/autoUpload/FileSystemRepository.kt
@@ -159,20 +159,19 @@ class FileSystemRepository(private val dao: FileSystemDao, private val context:
                 return
             }
 
+            val entity = dao.getFileByPathAndFolder(localPath, syncedFolder.id.toString())
+            val fileSentForUpload = (entity != null && entity.fileSentForUpload == 1)
+            if (fileSentForUpload) {
+                Log_OC.d(TAG, "File was sent for upload, checking if it changed...")
+            }
+
             val fileModified = (lastModified ?: file.lastModified())
-            val shouldSkipFileBasedOnFolderSettings = syncedFolder.shouldSkipFile(file, fileModified, creationTime)
-            if (shouldSkipFileBasedOnFolderSettings) {
+            if (syncedFolder.shouldSkipFile(file, fileModified, creationTime, fileSentForUpload)) {
                 return
             }
 
-            val entity = dao.getFileByPathAndFolder(localPath, syncedFolder.id.toString())
-            if (entity != null && entity.fileSentForUpload == 1) {
-                Log_OC.w(
-                    TAG,
-                    "file already uploaded path: $localPath, " +
-                        "syncedFolder: ${syncedFolder.localPath}, ${syncedFolder.id}"
-                )
-                return
+            if (fileSentForUpload) {
+                Log_OC.d(TAG, "File was sent for upload before but has changed, will re-upload: $localPath")
             }
 
             val crc = getFileChecksum(file)
@@ -182,7 +181,7 @@ class FileSystemRepository(private val dao: FileSystemDao, private val context:
                 localPath = localPath,
                 fileIsFolder = if (file.isDirectory) 1 else 0,
                 fileFoundRecently = System.currentTimeMillis(),
-                fileSentForUpload = 0,
+                fileSentForUpload = 0, // Reset to 0 to queue for upload
                 syncedFolderId = syncedFolder.id.toString(),
                 crc32 = crc?.toString(),
                 fileModified = fileModified
diff --git a/app/src/main/java/com/nextcloud/utils/extensions/SyncedFolderExtensions.kt b/app/src/main/java/com/nextcloud/utils/extensions/SyncedFolderExtensions.kt
index c7bdadfe6f54..7f8cac806f2f 100644
--- a/app/src/main/java/com/nextcloud/utils/extensions/SyncedFolderExtensions.kt
+++ b/app/src/main/java/com/nextcloud/utils/extensions/SyncedFolderExtensions.kt
@@ -22,7 +22,12 @@ private const val TAG = "SyncedFolderExtensions"
  * Determines whether a file should be skipped during auto-upload based on folder settings.
  */
 @Suppress("ReturnCount")
-fun SyncedFolder.shouldSkipFile(file: File, lastModified: Long, creationTime: Long?): Boolean {
+fun SyncedFolder.shouldSkipFile(
+    file: File,
+    lastModified: Long,
+    creationTime: Long?,
+    fileSentForUpload: Boolean
+): Boolean {
     Log_OC.d(TAG, "Checking file: ${file.name}, lastModified=$lastModified, lastScan=$lastScanTimestampMs")
 
     if (isExcludeHidden && file.isHidden) {
@@ -38,15 +43,19 @@ fun SyncedFolder.shouldSkipFile(file: File, lastModified: Long, creationTime: Lo
                 return true
             }
         } else {
-            Log_OC.w(TAG, "file sent for upload - cannot determine creation time: ${file.absolutePath}")
+            Log_OC.w(TAG, "file will be inserted to db - cannot determine creation time: ${file.absolutePath}")
             return false
         }
     }
 
-    // Skip files that haven't changed since last scan (already processed)
-    // BUT only if this is not the first scan
-    if (lastScanTimestampMs != -1L && lastModified < lastScanTimestampMs) {
-        Log_OC.d(TAG, "Skipping unchanged file (last modified < last scan): ${file.absolutePath}")
+    // Skip files that haven't changed since last scan ONLY if they were sent for upload
+    // AND only if this is not the first scan
+    if (fileSentForUpload && lastScanTimestampMs != -1L && lastModified < lastScanTimestampMs) {
+        Log_OC.d(
+            TAG,
+            "Skipping unchanged file that was already sent for upload (last modified < last scan): " +
+                "${file.absolutePath}"
+        )
         return true
     }
 
diff --git a/app/src/test/java/com/owncloud/android/utils/AutoUploadHelperTest.kt b/app/src/test/java/com/owncloud/android/utils/AutoUploadHelperTest.kt
index 993ee41a2915..a7aff50a8cc3 100644
--- a/app/src/test/java/com/owncloud/android/utils/AutoUploadHelperTest.kt
+++ b/app/src/test/java/com/owncloud/android/utils/AutoUploadHelperTest.kt
@@ -132,10 +132,10 @@ class AutoUploadHelperTest {
             type = MediaFolderType.CUSTOM
         )
 
-        val shouldSkipOldFile = folder.shouldSkipFile(oldFile, oldFileLastModified, null)
+        val shouldSkipOldFile = folder.shouldSkipFile(oldFile, oldFileLastModified, null, true)
         assertTrue(shouldSkipOldFile)
 
-        val shouldSkipNewFile = folder.shouldSkipFile(newFile, currentTime, null)
+        val shouldSkipNewFile = folder.shouldSkipFile(newFile, currentTime, null, false)
         assertTrue(!shouldSkipNewFile)
     }
 
@@ -157,10 +157,10 @@ class AutoUploadHelperTest {
             lastScanTimestampMs = currentTime
         }
 
-        val shouldSkipOldFile = folder.shouldSkipFile(oldFile, oldFileLastModified, null)
+        val shouldSkipOldFile = folder.shouldSkipFile(oldFile, oldFileLastModified, null, true)
         assertTrue(shouldSkipOldFile)
 
-        val shouldSkipNewFile = folder.shouldSkipFile(newFile, currentTime, null)
+        val shouldSkipNewFile = folder.shouldSkipFile(newFile, currentTime, null, false)
         assertTrue(!shouldSkipNewFile)
     }
 
@@ -305,10 +305,10 @@ class AutoUploadHelperTest {
             setEnabled(true, currentTime)
         }
 
-        val shouldSkipOldFile = folderSkipOld.shouldSkipFile(oldFile, oldFileLastModified, oldFileCreationTime)
+        val shouldSkipOldFile = folderSkipOld.shouldSkipFile(oldFile, oldFileLastModified, oldFileCreationTime, true)
         assertTrue(shouldSkipOldFile)
 
-        val shouldSkipNewFile = folderSkipOld.shouldSkipFile(newFile, newFileLastModified, newFileCreationTime)
+        val shouldSkipNewFile = folderSkipOld.shouldSkipFile(newFile, newFileLastModified, newFileCreationTime, false)
         assertTrue(!shouldSkipNewFile)
 
         val folderUploadAll = createTestFolder(
@@ -320,11 +320,11 @@ class AutoUploadHelperTest {
         }
 
         val shouldSkipOldFileIfAlsoUploadExistingFile =
-            folderUploadAll.shouldSkipFile(oldFile, oldFileLastModified, oldFileCreationTime)
+            folderUploadAll.shouldSkipFile(oldFile, oldFileLastModified, oldFileCreationTime, true)
         assertTrue(!shouldSkipOldFileIfAlsoUploadExistingFile)
 
         val shouldSkipNewFileIfAlsoUploadExistingFile =
-            folderUploadAll.shouldSkipFile(newFile, newFileLastModified, newFileCreationTime)
+            folderUploadAll.shouldSkipFile(newFile, newFileLastModified, newFileCreationTime, false)
         assertTrue(!shouldSkipNewFileIfAlsoUploadExistingFile)
     }
 }