diff --git a/files/ansible-playbooks/sot-updater.yml b/files/ansible-playbooks/sot-updater.yml
index 6a8ba4c..887f25d 100644
--- a/files/ansible-playbooks/sot-updater.yml
+++ b/files/ansible-playbooks/sot-updater.yml
@@ -81,19 +81,36 @@
           - "{{ (nb_preflight.stderr_lines | default(['<no stderr>'])) }}"
           - "raw stdout (joined): {{ nb_preflight.stdout | default('') | trim }}"
 
-    # --- Detect cloud failure (rc==3 or FAIL Cloud line) ---
     - name: "NB preflight | Detect cloud failure"
       when: nb_script.stat.exists
       delegate_to: localhost
       vars:
+        _out: "{{ (nb_preflight.stdout | default('') | regex_replace('\r','')) }}"
         _lines: >-
-          {{ (nb_preflight.stdout | default('') | regex_replace('\r','')) | split('\n') | map('trim') | list }}
+          {{ _out.split('\n') | map('trim') | list }}
         _cloud_fail_line: >-
           {{ (_lines | select('match', '^FAIL\\s+Cloud\\b') | list | last | default('')) }}
+        _error_line: >-
+          {{ (_lines | select('match', '^FAIL\\s+') | list | last | default('')) }}
         _rc_is_3: "{{ (nb_preflight.rc | default(1)) | int == 3 }}"
+        _cloud_error_type: >-
+          {%- if _error_line is search('network error')
+                and _error_line is search('500 error responses') -%}
+            cloud_http_500
+          {%- elif (_cloud_fail_line | length) > 0 -%}
+            cloud_logic
+          {%- elif _rc_is_3 -%}
+            cloud_other
+          {%- else -%}
+            none
+          {%- endif -%}
+        _cloud_retryable: >-
+          {{ _cloud_error_type not in ['cloud_http_500'] }}
       set_fact:
         cloud_fail_line: "{{ _cloud_fail_line }}"
         cloud_bad: "{{ _rc_is_3 or (( _cloud_fail_line | length ) > 0) }}"
+        cloud_error_type: "{{ _cloud_error_type }}"
+        cloud_retryable: "{{ _cloud_retryable }}"
 
     # --- Extract upgrade_cmd line if any ---
     - name: "NB preflight | Extract upgrade_cmd line"