diff --git a/CHANGES b/CHANGES
index f6b5847..5fcef2d 100644
--- a/CHANGES
+++ b/CHANGES
@@ -1,3 +1,7 @@
+1.16.1
+-----
+- Show the server's error reason and missing scan file details when an offline endpoint scan upload fails
+
 1.16.0
 -----
 - alerts-data-sources deactivate-batch: deactivate multiple alert data sources concurrently, either from a text file of connector IDs (`--config`) or every connector currently in `active`/`offline`/`update_failed` (`--all-active`)
diff --git a/intezer_analyze_cli/__init__.py b/intezer_analyze_cli/__init__.py
index 20f9c7e..4b2887f 100644
--- a/intezer_analyze_cli/__init__.py
+++ b/intezer_analyze_cli/__init__.py
@@ -1 +1 @@
-__version__ = '1.16.0'
+__version__ = '1.16.1'
diff --git a/intezer_analyze_cli/commands.py b/intezer_analyze_cli/commands.py
index af5817c..7de1d07 100644
--- a/intezer_analyze_cli/commands.py
+++ b/intezer_analyze_cli/commands.py
@@ -5,6 +5,7 @@
 from email.utils import parsedate_to_datetime
 
 import click
+import requests
 from intezer_sdk import api
 from intezer_sdk import consts as sdk_consts
 from intezer_sdk import errors as sdk_errors
@@ -310,6 +311,15 @@ def upload_offline_endpoint_scan(offline_scan_directory: str, force: bool = Fals
         click.echo(f'Analyze error: {e}')
         logger.exception('Failed to analyze offline scan')
         raise
+    except requests.HTTPError as error:
+        click.echo(f'Upload failed: {error}')
+        logger.exception('Failed to upload offline scan')
+        raise
+    except FileNotFoundError as error:
+        click.echo(f'Missing scan file: {error.filename}. Make sure the path is the scan output directory '
+                   'created by the scanner (scan_<computername>_<date>_<time>)')
+        logger.exception('Failed to upload offline scan, scan file is missing')
+        raise
     return endpoint_analysis.analysis_id
 
 
diff --git a/tests/unit/commands_test.py b/tests/unit/commands_test.py
index 998b757..55d55d6 100644
--- a/tests/unit/commands_test.py
+++ b/tests/unit/commands_test.py
@@ -12,6 +12,7 @@
 from unittest.mock import patch
 
 import click.exceptions
+import requests
 import intezer_sdk.endpoint_analysis
 import intezer_sdk.base_analysis
 from intezer_sdk import errors as sdk_errors
@@ -128,6 +129,41 @@ def test_offline_scan_upload(self):
             self.send_analyze_mock.assert_called_once()
             self.assertTrue(os.path.isfile(analysis_id_file_path))
 
+    def test_offline_scan_upload_echoes_server_error_when_http_error_is_raised(self):
+        # Arrange
+        create_global_api()
+        self.send_analyze_mock.side_effect = requests.HTTPError(
+            '409 Client Error: CONFLICT for url: https://analyze.intezer.com/scans, '
+            'server returns Windows scanner version 1.0.1.20 is not supported'
+        )
+        with tempfile.TemporaryDirectory() as root:
+            offline_scan_directory = self._create_temporary_directory_hierarchy(root)
+
+            # Act
+            with patch('intezer_analyze_cli.commands.click.echo') as echo_mock:
+                with self.assertRaises(requests.HTTPError):
+                    commands.upload_offline_endpoint_scan(offline_scan_directory)
+
+        # Assert
+        echoed_messages = ' '.join(str(echo_call.args[0]) for echo_call in echo_mock.call_args_list)
+        self.assertIn('Windows scanner version 1.0.1.20 is not supported', echoed_messages)
+
+    def test_offline_scan_upload_echoes_missing_file_when_scan_file_is_missing(self):
+        # Arrange
+        create_global_api()
+        self.send_analyze_mock.side_effect = FileNotFoundError(2, 'No such file or directory', 'scanner_info.json')
+        with tempfile.TemporaryDirectory() as root:
+            offline_scan_directory = self._create_temporary_directory_hierarchy(root)
+
+            # Act
+            with patch('intezer_analyze_cli.commands.click.echo') as echo_mock:
+                with self.assertRaises(FileNotFoundError):
+                    commands.upload_offline_endpoint_scan(offline_scan_directory)
+
+        # Assert
+        echoed_messages = ' '.join(str(echo_call.args[0]) for echo_call in echo_mock.call_args_list)
+        self.assertIn('scanner_info.json', echoed_messages)
+
     def test_offline_scan_do_not_upload_if_already_uploaded(self):
         # Arrange
         create_global_api()