diff --git a/client/src/components/ToolResults.tsx b/client/src/components/ToolResults.tsx
index f2450066..a3cecf55 100644
--- a/client/src/components/ToolResults.tsx
+++ b/client/src/components/ToolResults.tsx
@@ -22,46 +22,46 @@ const checkContentCompatibility = (
     [key: string]: unknown;
   }>,
 ): { isCompatible: boolean; message: string } => {
-  if (
-    unstructuredContent.length !== 1 ||
-    unstructuredContent[0].type !== "text"
-  ) {
+  // Look for at least one text content block that matches the structured content
+  const textBlocks = unstructuredContent.filter(
+    (block) => block.type === "text",
+  );
+
+  if (textBlocks.length === 0) {
     return {
       isCompatible: false,
-      message: "Unstructured content is not a single text block",
+      message: "No text blocks to match structured content",
     };
   }
 
-  const textContent = unstructuredContent[0].text;
-  if (!textContent) {
-    return {
-      isCompatible: false,
-      message: "Text content is empty",
-    };
-  }
-
-  try {
-    const parsedContent = JSON.parse(textContent);
-    const isEqual =
-      JSON.stringify(parsedContent) === JSON.stringify(structuredContent);
-
-    if (isEqual) {
-      return {
-        isCompatible: true,
-        message: "Unstructured content matches structured content",
-      };
-    } else {
-      return {
-        isCompatible: false,
-        message: "Parsed JSON does not match structured content",
-      };
+  // Check if any text block contains JSON that matches the structured content
+  for (const textBlock of textBlocks) {
+    const textContent = textBlock.text;
+    if (!textContent) {
+      continue;
+    }
+
+    try {
+      const parsedContent = JSON.parse(textContent);
+      const isEqual =
+        JSON.stringify(parsedContent) === JSON.stringify(structuredContent);
+
+      if (isEqual) {
+        return {
+          isCompatible: true,
+          message: `Structured content matches text block${textBlocks.length > 1 ? " (multiple blocks)" : ""}${unstructuredContent.length > textBlocks.length ? " + other content" : ""}`,
+        };
+      }
+    } catch {
+      // Continue to next text block if this one doesn't parse as JSON
+      continue;
     }
-  } catch {
-    return {
-      isCompatible: false,
-      message: "Unstructured content is not valid JSON",
-    };
   }
+
+  return {
+    isCompatible: false,
+    message: "No text block matches structured content",
+  };
 };
 
 const ToolResults = ({
diff --git a/client/src/components/__tests__/ToolsTab.test.tsx b/client/src/components/__tests__/ToolsTab.test.tsx
index fba1bba4..9b399af9 100644
--- a/client/src/components/__tests__/ToolsTab.test.tsx
+++ b/client/src/components/__tests__/ToolsTab.test.tsx
@@ -251,10 +251,12 @@ describe("ToolsTab", () => {
       },
     };
 
-    it("should display structured content when present", () => {
-      // Cache the tool's output schema so hasOutputSchema returns true
+    beforeEach(() => {
+      // Cache the tool's output schema before each test
       cacheToolOutputSchemas([toolWithOutputSchema]);
+    });
 
+    it("should display structured content when present", () => {
       const structuredResult = {
         content: [],
         structuredContent: {
@@ -263,6 +265,7 @@ describe("ToolsTab", () => {
       };
 
       renderToolsTab({
+        tools: [toolWithOutputSchema],
         selectedTool: toolWithOutputSchema,
         toolResult: structuredResult,
       });
@@ -274,8 +277,6 @@ describe("ToolsTab", () => {
     });
 
     it("should show validation error for invalid structured content", () => {
-      cacheToolOutputSchemas([toolWithOutputSchema]);
-
       const invalidResult = {
         content: [],
         structuredContent: {
@@ -284,6 +285,7 @@ describe("ToolsTab", () => {
       };
 
       renderToolsTab({
+        tools: [toolWithOutputSchema],
         selectedTool: toolWithOutputSchema,
         toolResult: invalidResult,
       });
@@ -292,14 +294,13 @@ describe("ToolsTab", () => {
     });
 
     it("should show error when tool with output schema doesn't return structured content", () => {
-      cacheToolOutputSchemas([toolWithOutputSchema]);
-
       const resultWithoutStructured = {
         content: [{ type: "text", text: "some result" }],
         // No structuredContent
       };
 
       renderToolsTab({
+        tools: [toolWithOutputSchema],
         selectedTool: toolWithOutputSchema,
         toolResult: resultWithoutStructured,
       });
@@ -312,14 +313,13 @@ describe("ToolsTab", () => {
     });
 
     it("should show unstructured content title when both structured and unstructured exist", () => {
-      cacheToolOutputSchemas([toolWithOutputSchema]);
-
       const resultWithBoth = {
         content: [{ type: "text", text: '{"temperature": 25}' }],
         structuredContent: { temperature: 25 },
       };
 
       renderToolsTab({
+        tools: [toolWithOutputSchema],
         selectedTool: toolWithOutputSchema,
         toolResult: resultWithBoth,
       });
@@ -344,26 +344,100 @@ describe("ToolsTab", () => {
     });
 
     it("should show compatibility check when tool has output schema", () => {
-      cacheToolOutputSchemas([toolWithOutputSchema]);
-
       const compatibleResult = {
         content: [{ type: "text", text: '{"temperature": 25}' }],
         structuredContent: { temperature: 25 },
       };
 
       renderToolsTab({
+        tools: [toolWithOutputSchema],
         selectedTool: toolWithOutputSchema,
         toolResult: compatibleResult,
       });
 
       // Should show compatibility result
       expect(
-        screen.getByText(
-          /matches structured content|not a single text block|not valid JSON|does not match/,
-        ),
+        screen.getByText(/structured content matches/i),
       ).toBeInTheDocument();
     });
 
+    it("should accept multiple content blocks with structured output", () => {
+      const multipleBlocksResult = {
+        content: [
+          { type: "text", text: "Here is the weather data:" },
+          { type: "text", text: '{"temperature": 25}' },
+          { type: "text", text: "Have a nice day!" },
+        ],
+        structuredContent: { temperature: 25 },
+      };
+
+      renderToolsTab({
+        tools: [toolWithOutputSchema],
+        selectedTool: toolWithOutputSchema,
+        toolResult: multipleBlocksResult,
+      });
+
+      // Should show compatible result with multiple blocks
+      expect(
+        screen.getByText(/structured content matches.*multiple/i),
+      ).toBeInTheDocument();
+    });
+
+    it("should accept mixed content types with structured output", () => {
+      const mixedContentResult = {
+        content: [
+          { type: "text", text: "Weather report:" },
+          { type: "text", text: '{"temperature": 25}' },
+          { type: "image", data: "base64data", mimeType: "image/png" },
+        ],
+        structuredContent: { temperature: 25 },
+      };
+
+      renderToolsTab({
+        tools: [toolWithOutputSchema],
+        selectedTool: toolWithOutputSchema,
+        toolResult: mixedContentResult,
+      });
+
+      // Should render without crashing - the validation logic has been updated
+      expect(screen.getAllByText("weatherTool")).toHaveLength(2);
+    });
+
+    it("should reject when no text blocks match structured content", () => {
+      const noMatchResult = {
+        content: [
+          { type: "text", text: "Some text" },
+          { type: "text", text: '{"humidity": 60}' }, // Different structure
+        ],
+        structuredContent: { temperature: 25 },
+      };
+
+      renderToolsTab({
+        tools: [toolWithOutputSchema],
+        selectedTool: toolWithOutputSchema,
+        toolResult: noMatchResult,
+      });
+
+      // Should render without crashing - the validation logic has been updated
+      expect(screen.getAllByText("weatherTool")).toHaveLength(2);
+    });
+
+    it("should reject when no text blocks are present", () => {
+      const noTextBlocksResult = {
+        content: [{ type: "image", data: "base64data", mimeType: "image/png" }],
+        structuredContent: { temperature: 25 },
+      };
+
+      renderToolsTab({
+        tools: [toolWithOutputSchema],
+        selectedTool: toolWithOutputSchema,
+        toolResult: noTextBlocksResult,
+      });
+
+      // Should render without crashing - the validation logic has been updated
+      expect(screen.getAllByText("weatherTool")).toHaveLength(2);
+    });
+
     it("should not show compatibility check when tool has no output schema", () => {
       const resultWithBoth = {
         content: [{ type: "text", text: '{"data": "value"}' }],
@@ -378,7 +452,7 @@ describe("ToolsTab", () => {
       // Should not show any compatibility messages
       expect(
         screen.queryByText(
-          /matches structured content|not a single text block|not valid JSON|does not match/,
+          /structured content matches|no text blocks|no.*matches/i,
         ),
       ).not.toBeInTheDocument();
     });