diff --git a/backend/app/routers/system.py b/backend/app/routers/system.py
index 294c7e7..b2cac38 100644
--- a/backend/app/routers/system.py
+++ b/backend/app/routers/system.py
@@ -354,7 +354,7 @@ def test_jira_connection(
     """
     from app.services.jira_service import (
         get_admin_jira_client, get_jira_url, has_admin_jira_configured,
-        get_admin_jira_email,
+        get_admin_jira_email, get_admin_jira_api_token, is_jira_enabled,
     )
 
     jira_url = get_jira_url(db)
@@ -362,12 +362,21 @@ def test_jira_connection(
         return {"status": "error", "message": "Jira URL is not configured.", "jira_url": ""}
 
     if not has_admin_jira_configured(db):
+        # has_admin_jira_configured() bundles 4 independent checks into one
+        # bool — report exactly which one(s) are actually missing instead of
+        # always blaming "Admin Email and Admin API Token" regardless of
+        # which check failed (e.g. URL/email/token can all be set while the
+        # "Enable Jira Integration" toggle itself is still off).
+        missing = []
+        if not is_jira_enabled(db):
+            missing.append("Jira integration is not enabled (toggle 'Enable Jira Integration' above)")
+        if not get_admin_jira_email(db):
+            missing.append("Admin Email is not set")
+        if not get_admin_jira_api_token(db):
+            missing.append("Admin API Token is not set")
         return {
             "status": "error",
-            "message": (
-                "Admin Jira credentials not configured. "
-                "Set the Admin Email and Admin API Token in the fields above."
-            ),
+            "message": "Cannot connect: " + "; ".join(missing) + ".",
             "jira_url": jira_url,
         }
 
diff --git a/backend/tests/test_jira_test_connection.py b/backend/tests/test_jira_test_connection.py
new file mode 100644
index 0000000..a578b6a
--- /dev/null
+++ b/backend/tests/test_jira_test_connection.py
@@ -0,0 +1,54 @@
+"""Tests for POST /system/jira-test's diagnostic message.
+
+Regression coverage for a real QA-reported bug: has_admin_jira_configured()
+bundles four independent checks (enabled, url, admin_email, admin_api_token)
+into one bool, but the error message always blamed "Admin Email and Admin
+API Token" regardless of which check actually failed. An admin who had set
+url/email/token correctly but never flipped the "Enable Jira Integration"
+toggle saw a misleading message pointing at the wrong fields.
+"""
+
+from app.models.system_config import SystemConfig
+
+
+def _set_config(db, key, value):
+    db.add(SystemConfig(key=key, value=value))
+
+
+def test_jira_test_reports_disabled_toggle_specifically(client, db, auth_headers):
+    """url/email/token all set, but jira.enabled is missing entirely —
+    the message must call out the toggle, not email/token."""
+    _set_config(db, "jira.url", "https://example.atlassian.net")
+    _set_config(db, "jira.admin_email", "admin@example.com")
+    _set_config(db, "jira.admin_api_token", "some-real-token")
+    db.commit()
+
+    resp = client.post("/api/v1/system/jira-test", headers=auth_headers)
+    assert resp.status_code == 200
+    body = resp.json()
+    assert body["status"] == "error"
+    assert "not enabled" in body["message"]
+    assert "Admin Email" not in body["message"]
+    assert "Admin API Token" not in body["message"]
+
+
+def test_jira_test_reports_missing_email_and_token_when_actually_missing(client, db, auth_headers):
+    _set_config(db, "jira.url", "https://example.atlassian.net")
+    _set_config(db, "jira.enabled", "true")
+    db.commit()
+
+    resp = client.post("/api/v1/system/jira-test", headers=auth_headers)
+    assert resp.status_code == 200
+    body = resp.json()
+    assert body["status"] == "error"
+    assert "Admin Email is not set" in body["message"]
+    assert "Admin API Token is not set" in body["message"]
+    assert "not enabled" not in body["message"]
+
+
+def test_jira_test_missing_url_reports_url_specifically(client, db, auth_headers):
+    resp = client.post("/api/v1/system/jira-test", headers=auth_headers)
+    assert resp.status_code == 200
+    body = resp.json()
+    assert body["status"] == "error"
+    assert "Jira URL is not configured" in body["message"]