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diff --git a/packages/xl-ai/src/api/formats/json/__snapshots__/json.test.ts/Add/__msw_snapshots__/openai.chat/gpt-4o-2024-08-06 (non-streaming)/add a link to google.com_1_a07b53b9e3645cc50e882d6a23d17c0c.json b/packages/xl-ai/src/api/formats/json/__snapshots__/json.test.ts/Add/__msw_snapshots__/openai.chat/gpt-4o-2024-08-06 (non-streaming)/add a link to google.com_1_a07b53b9e3645cc50e882d6a23d17c0c.json
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diff --git a/packages/xl-ai/src/api/formats/json/__snapshots__/json.test.ts/Add/__msw_snapshots__/openai.chat/gpt-4o-2024-08-06 (streaming)/add a link to google.com_1_3b0faf254f985c2234d441af7209d29a.json b/packages/xl-ai/src/api/formats/json/__snapshots__/json.test.ts/Add/__msw_snapshots__/openai.chat/gpt-4o-2024-08-06 (streaming)/add a link to google.com_1_3b0faf254f985c2234d441af7209d29a.json
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+    "headers": []
+  }
+}
\ No newline at end of file
diff --git a/packages/xl-ai/src/api/formats/json/__snapshots__/json.test.ts/Add/__msw_snapshots__/openai.chat/gpt-4o-2024-08-06 (streaming)/add a link to google.com_1_fbb9d88d76ae07c1200114cb1bb24e44.json b/packages/xl-ai/src/api/formats/json/__snapshots__/json.test.ts/Add/__msw_snapshots__/openai.chat/gpt-4o-2024-08-06 (streaming)/add a link to google.com_1_fbb9d88d76ae07c1200114cb1bb24e44.json
new file mode 100644
index 0000000000..70f3866974
--- /dev/null
+++ b/packages/xl-ai/src/api/formats/json/__snapshots__/json.test.ts/Add/__msw_snapshots__/openai.chat/gpt-4o-2024-08-06 (streaming)/add a link to google.com_1_fbb9d88d76ae07c1200114cb1bb24e44.json	
@@ -0,0 +1,15 @@
+{
+  "request": {
+    "method": "POST",
+    "url": "https://api.openai.com/v1/chat/completions",
+    "body": "{\"model\":\"gpt-4o-2024-08-06\",\"temperature\":0,\"messages\":[{\"role\":\"system\",\"content\":\"You're manipulating a text document using JSON blocks. \\n        Make sure to follow the json schema provided. When referencing ids they MUST be EXACTLY the same (including the trailing $). \\n        This is the document as an array of JSON blocks (the cursor is BETWEEN two blocks as indicated by cursor: true):\"},{\"role\":\"system\",\"content\":\"[{\\\"id\\\":\\\"ref1$\\\",\\\"block\\\":{\\\"id\\\":\\\"ref1\\\",\\\"type\\\":\\\"paragraph\\\",\\\"props\\\":{\\\"textColor\\\":\\\"default\\\",\\\"backgroundColor\\\":\\\"default\\\",\\\"textAlignment\\\":\\\"left\\\"},\\\"content\\\":[{\\\"type\\\":\\\"text\\\",\\\"text\\\":\\\"Hello, world!\\\",\\\"styles\\\":{}}]}},{\\\"cursor\\\":true},{\\\"id\\\":\\\"ref2$\\\",\\\"block\\\":{\\\"id\\\":\\\"ref2\\\",\\\"type\\\":\\\"paragraph\\\",\\\"props\\\":{\\\"textColor\\\":\\\"default\\\",\\\"backgroundColor\\\":\\\"default\\\",\\\"textAlignment\\\":\\\"left\\\"},\\\"content\\\":[{\\\"type\\\":\\\"text\\\",\\\"text\\\":\\\"How are you?\\\",\\\"styles\\\":{}}]}}]\"},{\"role\":\"system\",\"content\":\"The user asks you to do the following:\"},{\"role\":\"system\",\"content\":\"First, determine what part of the document the user is talking about. 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{\"id\":\"chatcmpl-CCW1Jwd5xrbau2u1GbBvgTMd3dmUA\",\"object\":\"chat.completion.chunk\",\"created\":1757099057,\"model\":\"gpt-4o-2024-08-06\",\"service_tier\":\"default\",\"system_fingerprint\":\"fp_cbf1785567\",\"choices\":[{\"index\":0,\"delta\":{\"tool_calls\":[{\"index\":0,\"function\":{\"arguments\":\"]}\"}}]},\"logprobs\":null,\"finish_reason\":null}],\"obfuscation\":\"R\"}\n\ndata: {\"id\":\"chatcmpl-CCW1Jwd5xrbau2u1GbBvgTMd3dmUA\",\"object\":\"chat.completion.chunk\",\"created\":1757099057,\"model\":\"gpt-4o-2024-08-06\",\"service_tier\":\"default\",\"system_fingerprint\":\"fp_cbf1785567\",\"choices\":[{\"index\":0,\"delta\":{},\"logprobs\":null,\"finish_reason\":\"stop\"}],\"obfuscation\":\"fanYK3E\"}\n\ndata: [DONE]\n\n",
+    "headers": []
+  }
+}
\ No newline at end of file
diff --git a/packages/xl-ai/src/api/formats/json/tools/validate.ts b/packages/xl-ai/src/api/formats/json/tools/validate.ts
index 10d95d0599..41b1ce1ab7 100644
--- a/packages/xl-ai/src/api/formats/json/tools/validate.ts
+++ b/packages/xl-ai/src/api/formats/json/tools/validate.ts
@@ -27,7 +27,9 @@ function validateInlineContent(content: any, editor: any): boolean {
       return false;
     }
 
-    return validateInlineContent(content.content, editor);
+    return content.content.every((child: any) =>
+      validateInlineContent(child, editor),
+    );
   }
 
   // TODO: custom ic content
diff --git a/packages/xl-ai/src/testUtil/cases/addOperationTestCases.ts b/packages/xl-ai/src/testUtil/cases/addOperationTestCases.ts
index 8d1179d918..67d9958577 100644
--- a/packages/xl-ai/src/testUtil/cases/addOperationTestCases.ts
+++ b/packages/xl-ai/src/testUtil/cases/addOperationTestCases.ts
@@ -99,4 +99,39 @@ export const addOperationTestCases: DocumentOperationTestCase[] = [
     ],
     userPrompt: `write a new paragraph with the text 'You look great today!'`,
   },
+  {
+    editor: getSimpleEditor,
+    description: "add a link to google.com",
+    baseToolCalls: [
+      {
+        type: "add",
+        blocks: [
+          {
+            type: "paragraph",
+            content: [
+              {
+                type: "text",
+                text: "Check this out ",
+              },
+              {
+                type: "link",
+                content: [
+                  {
+                    type: "text",
+                    text: "here",
+                    styles: {},
+                  },
+                ],
+                href: "https://www.google.com",
+              },
+            ],
+          },
+        ],
+        referenceId: "ref2",
+        position: "after",
+      },
+    ],
+    userPrompt:
+      "add a paragraph with the text 'Check this out' and a link with text 'here' to 'https://www.google.com' after the last sentence",
+  },
 ];