docs(email): clarify Outlook password auth failures

Co-authored-by: Alexandre Teixeira <111787685+alteixeira20@users.noreply.github.com>

routes/email_helpers.py

@@ -71,6 +71,38 @@ def _send_smtp_message(cfg: dict, from_addr: str, recipients: list[str], message
         smtp.sendmail(from_addr, recipients, message)
 
 
+def _friendly_email_auth_error(protocol: str, host: str, error: object) -> str:
+    """Return a clearer setup error for known provider auth policies."""
+    raw = str(error or "")
+    lower = raw.lower()
+    host_lower = (host or "").lower()
+    microsoft_host = any(
+        marker in host_lower
+        for marker in (
+            "outlook.office365.com",
+            "smtp.office365.com",
+            "office365.com",
+            "outlook.com",
+            "hotmail.com",
+            "live.com",
+        )
+    )
+    microsoft_basic_auth_failure = (
+        "5.7.139" in lower
+        or "basic authentication is disabled" in lower
+        or ("authenticate failed" in lower and microsoft_host)
+        or ("authentication unsuccessful" in lower and microsoft_host)
+    )
+    if microsoft_basic_auth_failure:
+        return (
+            "Microsoft no longer accepts normal mailbox passwords for "
+            "Outlook/Office 365 IMAP/SMTP in most accounts. Odysseus "
+            "does not support Microsoft OAuth/Graph mail yet, so Outlook "
+            "accounts cannot be added with this password form."
+        )
+    return raw[:200]
+
+
 def _strip_think(text: str) -> str:
     """Email-flavored think strip — thin wrapper over the central helper.
 

routes/email_routes.py

@@ -48,6 +48,7 @@ from routes.email_helpers import (
     _extract_attachment_to_disk, _extract_html, _extract_text,
     _fetch_sender_thread_context, _pre_retrieve_context,
     _EMAIL_REPLY_SYS_PROMPT_BASE, _POOL_HOOKS,
+    _friendly_email_auth_error,
     SendEmailRequest, ExtractStyleRequest,
     ATTACHMENTS_DIR, COMPOSE_UPLOADS_DIR, SCHEDULED_DB,
     attachment_extract_dir, _email_cache_owner_clause,
@@ -3163,7 +3164,7 @@ def setup_email_routes():
                     try: conn.logout()
                     except Exception: pass
             except Exception as e:
-                imap_result = {"ok": False, "error": str(e)[:200]}
+                imap_result = {"ok": False, "error": _friendly_email_auth_error("IMAP", imap_host, e)}
 
         smtp_host = (body.get("smtp_host") or "").strip()
         if smtp_host:
@@ -3185,7 +3186,7 @@ def setup_email_routes():
                     try: smtp.quit()
                     except Exception: pass
             except Exception as e:
-                smtp_result = {"ok": False, "error": str(e)[:200]}
+                smtp_result = {"ok": False, "error": _friendly_email_auth_error("SMTP", smtp_host, e)}
 
         return {
             "ok": imap_result["ok"] and (smtp_result is None or smtp_result["ok"]),