diff --git a/cms/djangoapps/contentstore/tasks.py b/cms/djangoapps/contentstore/tasks.py
index 25ed8596b7..1ad50c68e6 100644
--- a/cms/djangoapps/contentstore/tasks.py
+++ b/cms/djangoapps/contentstore/tasks.py
@@ -417,7 +417,7 @@ def import_olx(self, user_id, course_key_string, archive_path, archive_name, lan
             return User.objects.get(pk=user_id)
         except User.DoesNotExist as exc:
             with translation_language(language):
-                self.status.fail(_('Unknown User ID: {0}').format(user_id))
+                self.status.fail(_('User permission denied.'))
             LOGGER.error(f'{log_prefix}: Unknown User: {user_id}')
             monitor_import_failure(courselike_key, current_step, exception=exc)
             return
@@ -428,7 +428,7 @@ def import_olx(self, user_id, course_key_string, archive_path, archive_name, lan
         if not has_access:
             message = f'User permission denied: {user.username}'
             with translation_language(language):
-                self.status.fail(_('Permission denied'))
+                self.status.fail(_('Permission denied. You do not have write access to this course.'))
             LOGGER.error(f'{log_prefix}: {message}')
             monitor_import_failure(courselike_key, current_step, message=message)
         return has_access
@@ -452,7 +452,7 @@ def import_olx(self, user_id, course_key_string, archive_path, archive_name, lan
         if not archive_path_exists:
             message = f'Uploaded file {archive_path} not found'
             with translation_language(language):
-                self.status.fail(_('Tar file not found'))
+                self.status.fail(_('Uploaded Tar file not found. Try again.'))
             LOGGER.error(f'{log_prefix}: {message}')
             monitor_import_failure(courselike_key, current_step, message=message)
         return archive_path_exists
@@ -557,7 +557,7 @@ def import_olx(self, user_id, course_key_string, archive_path, archive_name, lan
             shutil.rmtree(course_dir)
             LOGGER.info(f'{log_prefix}: Temp data cleared')
 
-        self.status.fail(str(exception))
+        self.status.fail(_('An Unknown error occurred during the unpacking step.'))
         LOGGER.exception(f'{log_prefix}: Unknown error while unpacking', exc_info=True)
         monitor_import_failure(courselike_key, current_step, exception=exception)
         return
@@ -601,7 +601,8 @@ def import_olx(self, user_id, course_key_string, archive_path, archive_name, lan
             load_error_modules=False,
             static_content_store=contentstore(),
             target_id=courselike_key,
-            verbose=True
+            verbose=True,
+            status=self.status
         )
 
         new_location = courselike_items[0].location
@@ -611,8 +612,9 @@ def import_olx(self, user_id, course_key_string, archive_path, archive_name, lan
         set_custom_attribute('course_import_completed', True)
     except Exception as exception:  # pylint: disable=broad-except
         msg = str(exception)
-        LOGGER.exception(f'{log_prefix}: Unknown error while updating course {msg}')
-        self.status.fail(msg)
+        LOGGER.exception(f'{log_prefix}: Unknown error while importing course {msg}')
+        if self.status.state != UserTaskStatus.FAILED:
+            self.status.fail(_('Unknown error while importing course.'))
         monitor_import_failure(courselike_key, current_step, exception=exception)
     finally:
         if course_dir.isdir():
diff --git a/cms/djangoapps/contentstore/views/import_export.py b/cms/djangoapps/contentstore/views/import_export.py
index 246771219f..f9125d8936 100644
--- a/cms/djangoapps/contentstore/views/import_export.py
+++ b/cms/djangoapps/contentstore/views/import_export.py
@@ -253,6 +253,7 @@ def import_status_handler(request, course_key_string, filename=None):
     args = {'course_key_string': course_key_string, 'archive_name': filename}
     name = CourseImportTask.generate_name(args)
     task_status = UserTaskStatus.objects.filter(name=name)
+    message = ''
     for status_filter in STATUS_FILTERS:
         task_status = status_filter().filter_queryset(request, task_status, import_status_handler)
     task_status = task_status.order_by('-created').first()
@@ -267,10 +268,13 @@ def import_status_handler(request, course_key_string, filename=None):
         status = 4
     elif task_status.state in (UserTaskStatus.FAILED, UserTaskStatus.CANCELED):
         status = max(-(task_status.completed_steps + 1), -3)
+        artifact = UserTaskArtifact.objects.filter(name='Error', status=task_status).order_by('-created').first()
+        if artifact:
+            message = artifact.text
     else:
         status = min(task_status.completed_steps + 1, 3)
 
-    return JsonResponse({"ImportStatus": status})
+    return JsonResponse({"ImportStatus": status, "Message": message})
 
 
 def send_tarball(tarball, size):
diff --git a/cms/static/js/features/import/views/import.js b/cms/static/js/features/import/views/import.js
index 928071eae5..8bd9f91ed7 100644
--- a/cms/static/js/features/import/views/import.js
+++ b/cms/static/js/features/import/views/import.js
@@ -240,7 +240,7 @@ define(
              *
              * @param {int} [stage=0] Starting stage.
              */
-            pollStatus: function(stage) {
+            pollStatus: function(stage, message) {
                 if (current.state !== STATE.IN_PROGRESS) {
                     return;
                 }
@@ -250,13 +250,13 @@ define(
                 if (current.stage === STAGE.SUCCESS) {
                     success();
                 } else if (current.stage < STAGE.UPLOADING) { // Failed
-                    error(gettext('Error importing course'));
+                    error(message || gettext('Error importing course'));
                 } else { // In progress
                     updateFeedbackList();
 
                     $.getJSON(file.url, function(data) {
                         timeout.id = setTimeout(function() {
-                            this.pollStatus(data.ImportStatus);
+                            this.pollStatus(data.ImportStatus, data.Message);
                         }.bind(this), timeout.delay);
                     }.bind(this));
                 }
@@ -292,7 +292,7 @@ define(
                     if (current.stage !== STAGE.UPLOADING) {
                         current.state = STATE.IN_PROGRESS;
 
-                        this.pollStatus(current.stage);
+                        this.pollStatus(current.stage, data.Message);
                     } else {
                         // An import in the upload stage cannot be resumed
                         error(gettext('There was an error with the upload'));
diff --git a/common/lib/xmodule/xmodule/modulestore/xml_importer.py b/common/lib/xmodule/xmodule/modulestore/xml_importer.py
index 2f6a31b2e9..f4a145e458 100644
--- a/common/lib/xmodule/xmodule/modulestore/xml_importer.py
+++ b/common/lib/xmodule/xmodule/modulestore/xml_importer.py
@@ -30,6 +30,7 @@ import re
 from abc import abstractmethod
 
 import xblock
+from django.utils.translation import ugettext as _
 from lxml import etree
 from opaque_keys.edx.keys import UsageKey
 from opaque_keys.edx.locator import LibraryLocator
@@ -233,6 +234,7 @@ class ImportManager:
             create_if_not_present=False, raise_on_failure=False,
             static_content_subdir=DEFAULT_STATIC_CONTENT_SUBDIR,
             python_lib_filename='python_lib.zip',
+            status=None
     ):
         self.store = store
         self.user_id = user_id
@@ -257,6 +259,7 @@ class ImportManager:
             xblock_select=store.xblock_select,
             target_course_id=target_id,
         )
+        self.status = status
         self.logger, self.errors = make_error_tracker()
 
     def preflight(self):
@@ -362,6 +365,8 @@ class ImportManager:
             monitor_import_failure(course_id, 'Updating', exception=exc)
             logging.exception(f'Course import {course_id}: Error while parsing asset xml.')
             if self.raise_on_failure:  # lint-amnesty, pylint: disable=no-else-raise
+                if self.status:
+                    self.status.fail(_('Error while parsing xml for {}').format(assets_filename))
                 raise
             else:
                 return
@@ -479,6 +484,12 @@ class ImportManager:
                         log.exception(
                             f'Course import {dest_id}: failed to import module location {child.location}'
                         )
+                        if self.status:
+                            self.status.fail(
+                                _('Failed to import module: {} at location: {}').format(
+                                    child.display_name, child.location
+                                )
+                            )
                         raise
 
                     depth_first(child)
@@ -502,6 +513,12 @@ class ImportManager:
             except Exception:
                 msg = f'Course import {dest_id}: failed to import module location {leftover}'
                 log.error(msg)
+                if self.status:
+                    self.status.fail(
+                        _('Failed to import module: {} at location: {}').format(
+                            leftover.display_name, leftover.location
+                        )
+                    )
                 raise
 
     def run_imports(self):
@@ -588,6 +605,10 @@ class CourseImportManager(ImportManager):
                     "Skipping import of course with id, %s, "
                     "since it collides with an existing one", dest_id
                 )
+                if self.status:
+                    self.status.fail(
+                        _('Aborting import because a course with this id: {} already exists.').format(dest_id)
+                    )
                 raise
 
         return dest_id, runtime
@@ -697,6 +718,8 @@ class LibraryImportManager(ImportManager):
                     "Skipping import of Library with id %s, "
                     "since it collides with an existing one", dest_id
                 )
+                if self.status:
+                    self.status.fail(_('Aborting import since a library with this id already exists.'))
                 raise
 
         return dest_id, runtime