diff --git a/app/src/main/java/fr/free/nrw/commons/contributions/Contribution.kt b/app/src/main/java/fr/free/nrw/commons/contributions/Contribution.kt
index be763fe8a6..64b405a4c5 100644
--- a/app/src/main/java/fr/free/nrw/commons/contributions/Contribution.kt
+++ b/app/src/main/java/fr/free/nrw/commons/contributions/Contribution.kt
@@ -28,6 +28,9 @@ data class Contribution constructor(
     var dateCreatedSource: String? = null,
     var wikidataPlace: WikidataPlace? = null,
     var chunkInfo: ChunkInfo? = null,
+    // add error message to keep track of error message for failed upload
+    var errorMessage: String? = null,
+    var exceptionMessage: String? = null,
     /**
      * @return array list of entityids for the depictions
      */
diff --git a/app/src/main/java/fr/free/nrw/commons/contributions/ContributionsFragment.java b/app/src/main/java/fr/free/nrw/commons/contributions/ContributionsFragment.java
index 9b66556fc8..627b2ff8bd 100644
--- a/app/src/main/java/fr/free/nrw/commons/contributions/ContributionsFragment.java
+++ b/app/src/main/java/fr/free/nrw/commons/contributions/ContributionsFragment.java
@@ -43,6 +43,7 @@
 import fr.free.nrw.commons.notification.NotificationController;
 import fr.free.nrw.commons.profile.ProfileActivity;
 import fr.free.nrw.commons.theme.BaseActivity;
+import java.util.Arrays;
 import java.util.Date;
 import java.util.List;
 import java.util.Map;
@@ -116,6 +117,19 @@ public class ContributionsFragment
     @Inject
     SessionManager sessionManager;
 
+
+    private final List<String> STASH_ERROR_CODES = Arrays.asList(
+        "file path is null",
+        "upload to stash failed"
+    );
+
+    private final List<String> STASH_EXCEPTIONS = Arrays.asList(
+        "StashUploadException",
+        "IOException"
+    );
+
+
+
     private LatLng curLatLng;
 
     private boolean isFragmentAttachedBefore = false;
@@ -670,12 +684,16 @@ public void retryUpload(Contribution contribution) {
                 /* Limit the number of retries for a failed upload
                    to handle cases like invalid filename as such uploads
                    will never be successful */
-                if(retries < MAX_RETRIES) {
+                if (contribution.getErrorMessage() != null && isGenuineError(contribution)) {
+                    // we have a genuine error here therefore no retry
+                    // TODO: notify user of error
+
+                } else if(retries < MAX_RETRIES) {
                     contribution.setRetries(retries + 1);
                     Timber.d("Retried uploading %s %d times", contribution.getMedia().getFilename(), retries + 1);
                     restartUpload(contribution);
                 } else {
-                    // TODO: Show the exact reason for failure
+                    // TODO: notify user of error
                     Toast.makeText(getContext(),
                         R.string.retry_limit_reached, Toast.LENGTH_SHORT).show();
                 }
@@ -686,6 +704,27 @@ public void retryUpload(Contribution contribution) {
             ViewUtil.showLongToast(getContext(), R.string.this_function_needs_network_connection);
         }
 
+    }
+    /**
+     * Check if the error that occurs is a genuine error
+     * @param contribution contribution to be retried
+     */
+    public boolean isGenuineError(Contribution contribution) {
+
+        //check against array for genuine errors
+        for (String error : STASH_ERROR_CODES) {
+            if (contribution.getErrorMessage().contains(error)) {
+                return true;
+            }
+        }
+
+        for (String error : STASH_EXCEPTIONS) {
+            if (contribution.getExceptionMessage().contains(error)) {
+                return true;
+            }
+        }
+        return false;
+
     }
 
     /**
diff --git a/app/src/main/java/fr/free/nrw/commons/upload/worker/UploadWorker.kt b/app/src/main/java/fr/free/nrw/commons/upload/worker/UploadWorker.kt
index 864e3149ad..f9c1e57b52 100644
--- a/app/src/main/java/fr/free/nrw/commons/upload/worker/UploadWorker.kt
+++ b/app/src/main/java/fr/free/nrw/commons/upload/worker/UploadWorker.kt
@@ -297,8 +297,10 @@ class UploadWorker(var appContext: Context, workerParams: WorkerParameters) :
      */
     @SuppressLint("StringFormatInvalid")
     private suspend fun uploadContribution(contribution: Contribution) {
+        contribution.errorMessage = null
         if (contribution.localUri == null || contribution.localUri.path == null) {
             Timber.e("""upload: ${contribution.media.filename} failed, file path is null""")
+            contribution.errorMessage = "file path is null"
         }
 
         val media = contribution.media
@@ -378,6 +380,9 @@ class UploadWorker(var appContext: Context, workerParams: WorkerParameters) :
 
                         } else {
                             Timber.e("Stash Upload failed")
+                            if (uploadResult != null && contribution.errorMessage == null) {
+                                contribution.errorMessage = uploadResult.result
+                            }
                             showFailedNotification(contribution)
                             contribution.state = Contribution.STATE_FAILED
                             contribution.chunkInfo = null
@@ -385,6 +390,10 @@ class UploadWorker(var appContext: Context, workerParams: WorkerParameters) :
 
                         }
                     }catch (exception : Exception){
+                        if (contribution.errorMessage == null) {
+                            contribution.errorMessage = "upload from stash failed with exception"
+                        }
+                        contribution.exceptionMessage = exception.toString()
                         Timber.e(exception)
                         Timber.e("Upload from stash failed for contribution : $filename")
                         showFailedNotification(contribution)
@@ -401,6 +410,9 @@ class UploadWorker(var appContext: Context, workerParams: WorkerParameters) :
                     contributionDao.saveSynchronous(contribution)
                 }
                 else -> {
+                    if (contribution.errorMessage == null) {
+                        contribution.errorMessage = "upload to stash failed"
+                    }
                     Timber.e("""upload file to stash failed with status: ${stashUploadResult.state}""")
                     showFailedNotification(contribution)
                     contribution.state = Contribution.STATE_FAILED
@@ -409,6 +421,10 @@ class UploadWorker(var appContext: Context, workerParams: WorkerParameters) :
                 }
             }
         }catch (exception: Exception){
+            if (contribution.errorMessage == null) {
+                contribution.errorMessage = "upload to stash failed with exception"
+            }
+            contribution.exceptionMessage = exception.toString()
             Timber.e(exception)
             Timber.e("Stash upload failed for contribution: $filename")
             showFailedNotification(contribution)