diff --git a/apps/web/src/components/tool-set-selector.tsx b/apps/web/src/components/tool-set-selector.tsx
index 7c3601326e..0077e0bde3 100644
--- a/apps/web/src/components/tool-set-selector.tsx
+++ b/apps/web/src/components/tool-set-selector.tsx
@@ -315,14 +315,22 @@ export function ToolSetSelector({
 
   const connectionTools = selectedConnectionData?.tools ?? [];
 
-  // Check if specific tool is enabled
+  // Check if specific tool is enabled. A ["*"] grant means "all tools".
   const isToolSelected = (connectionId: string, toolName: string): boolean => {
-    return toolSet[connectionId]?.includes(toolName) ?? false;
+    const set = toolSet[connectionId];
+    if (!set) return false;
+    return set.includes("*") || set.includes(toolName);
   };
 
   // Toggle a single tool
   const toggleTool = (connectionId: string, toolName: string) => {
-    const currentTools = toolSet[connectionId] ?? [];
+    const rawTools = toolSet[connectionId] ?? [];
+    // Expand an "all tools" sentinel to concrete names first, so toggling one
+    // tool off leaves the rest selected. connectionTools is loaded for the open
+    // (selected) connection, which is the only one whose tools can be toggled.
+    const currentTools = rawTools.includes("*")
+      ? connectionTools.map((tt) => tt.name)
+      : rawTools;
     const isSelected = currentTools.includes(toolName);
 
     const newToolSet = { ...toolSet };
@@ -351,9 +359,11 @@ export function ToolSetSelector({
 
     const currentTools = toolSet[connectionId] ?? [];
     const allToolNames = tools.map((t) => t.name);
+    // A ["*"] grant counts as everything selected.
     const allSelected =
-      currentTools.length > 0 &&
-      allToolNames.every((name) => currentTools.includes(name));
+      currentTools.includes("*") ||
+      (currentTools.length > 0 &&
+        allToolNames.every((name) => currentTools.includes(name)));
 
     const newToolSet = { ...toolSet };
 
@@ -453,7 +463,12 @@ export function ToolSetSelector({
               {filteredConnections.map((connection) => {
                 const isSelected = selectedConnectionId === connection.id;
                 const totalTools = isSelected ? connectionTools.length : 0;
-                const activeTools = toolSet[connection.id]?.length ?? 0;
+                const rawSet = toolSet[connection.id];
+                // "*" means all tools — reflect the full count once known.
+                const activeTools =
+                  rawSet?.includes("*") && isSelected
+                    ? connectionTools.length
+                    : (rawSet?.length ?? 0);
 
                 return (
                   <ConnectionItem
diff --git a/apps/web/src/views/settings/org-role-detail.tsx b/apps/web/src/views/settings/org-role-detail.tsx
index c480afef00..4c1b26097f 100644
--- a/apps/web/src/views/settings/org-role-detail.tsx
+++ b/apps/web/src/views/settings/org-role-detail.tsx
@@ -1087,19 +1087,19 @@ function convertRoleToFormData(
   const toolSet: Record<string, string[]> = {};
   for (const [key, tools] of Object.entries(permission)) {
     if (key === "self" || key === "models") continue;
+    // Keep the RAW grant, including a ["*"] "all tools" sentinel. The
+    // connection LIST endpoint omits `tools`, so expanding "*" here yields []
+    // — which renders the connection as unchecked AND destroys the grant on the
+    // next save. ToolSetSelector understands "*" directly, so preserve it.
     if (key === "*") {
+      // Grant applies to every connection.
       for (const conn of connections) {
-        toolSet[conn.id] = tools.includes("*")
-          ? (conn.tools?.map((t) => t.name) ?? [])
-          : tools;
+        toolSet[conn.id] = tools;
       }
     } else {
-      const conn = connections.find((c) => c.id === key);
-      if (conn) {
-        toolSet[key] = tools.includes("*")
-          ? (conn.tools?.map((t) => t.name) ?? [])
-          : tools;
-      }
+      // Preserve unconditionally — even if the connection isn't in the current
+      // (possibly paginated) list, so a re-save round-trips instead of dropping.
+      toolSet[key] = tools;
     }
   }