diff --git a/client/src/components/ToolResults.tsx b/client/src/components/ToolResults.tsx
index c6d90700..661507aa 100644
--- a/client/src/components/ToolResults.tsx
+++ b/client/src/components/ToolResults.tsx
@@ -19,46 +19,44 @@ 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 content blocks found 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: `Found matching JSON content (${textBlocks.length > 1 ? 'among multiple text blocks' : 'in single text block'})${unstructuredContent.length > textBlocks.length ? ' with additional content blocks' : ''}`,
+        };
+      }
+    } 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 content block contains JSON matching structured content",
+  };
 };
 
 const ToolResults = ({ toolResult, selectedTool }: ToolResultsProps) => {
diff --git a/client/src/components/__tests__/ToolResults.test.tsx b/client/src/components/__tests__/ToolResults.test.tsx
new file mode 100644
index 00000000..be4de4ec
--- /dev/null
+++ b/client/src/components/__tests__/ToolResults.test.tsx
@@ -0,0 +1,185 @@
+import { render, screen } from "@testing-library/react";
+import "@testing-library/jest-dom";
+import { describe, it, beforeEach } from "@jest/globals";
+import ToolResults from "../ToolResults";
+import { Tool } from "@modelcontextprotocol/sdk/types.js";
+import { cacheToolOutputSchemas } from "@/utils/schemaUtils";
+
+describe("ToolResults", () => {
+  const mockTool: Tool = {
+    name: "testTool",
+    description: "Test tool",
+    inputSchema: {
+      type: "object",
+      properties: {},
+    },
+    outputSchema: {
+      type: "object",
+      properties: {
+        result: { type: "string" },
+      },
+      required: ["result"],
+    },
+  };
+
+  beforeEach(() => {
+    cacheToolOutputSchemas([mockTool]);
+  });
+
+  describe("Content Compatibility Validation", () => {
+    it("should accept single text block with matching JSON", () => {
+      const toolResult = {
+        content: [{ type: "text", text: '{"result": "success"}' }],
+        structuredContent: { result: "success" },
+      };
+
+      render(<ToolResults toolResult={toolResult} selectedTool={mockTool} />);
+
+      expect(screen.getByText(/Found matching JSON content.*in single text block/)).toBeInTheDocument();
+    });
+
+    it("should accept multiple text blocks with one matching JSON", () => {
+      const toolResult = {
+        content: [
+          { type: "text", text: "Processing..." },
+          { type: "text", text: '{"result": "success"}' },
+          { type: "text", text: "Done!" },
+        ],
+        structuredContent: { result: "success" },
+      };
+
+      render(<ToolResults toolResult={toolResult} selectedTool={mockTool} />);
+
+      expect(screen.getByText(/Found matching JSON content.*among multiple text blocks/)).toBeInTheDocument();
+    });
+
+    it("should accept mixed content types with matching JSON", () => {
+      const toolResult = {
+        content: [
+          { type: "text", text: "Result:" },
+          { type: "text", text: '{"result": "success"}' },
+          { type: "image", data: "base64data", mimeType: "image/png" },
+          { type: "resource", resource: { uri: "file://test.txt" } },
+        ],
+        structuredContent: { result: "success" },
+      };
+
+      render(<ToolResults toolResult={toolResult} selectedTool={mockTool} />);
+
+      expect(screen.getByText(/Found matching JSON content.*with additional content blocks/)).toBeInTheDocument();
+    });
+
+    it("should reject when no text blocks are present", () => {
+      const toolResult = {
+        content: [
+          { type: "image", data: "base64data", mimeType: "image/png" },
+        ],
+        structuredContent: { result: "success" },
+      };
+
+      render(<ToolResults toolResult={toolResult} selectedTool={mockTool} />);
+
+      expect(screen.getByText(/No text content blocks found to match structured content/)).toBeInTheDocument();
+    });
+
+    it("should reject when no text blocks contain matching JSON", () => {
+      const toolResult = {
+        content: [
+          { type: "text", text: "Some text" },
+          { type: "text", text: '{"different": "data"}' },
+        ],
+        structuredContent: { result: "success" },
+      };
+
+      render(<ToolResults toolResult={toolResult} selectedTool={mockTool} />);
+
+      expect(screen.getByText(/No text content block contains JSON matching structured content/)).toBeInTheDocument();
+    });
+
+    it("should reject when text blocks contain invalid JSON", () => {
+      const toolResult = {
+        content: [
+          { type: "text", text: "Not JSON" },
+          { type: "text", text: '{"invalid": json}' },
+        ],
+        structuredContent: { result: "success" },
+      };
+
+      render(<ToolResults toolResult={toolResult} selectedTool={mockTool} />);
+
+      expect(screen.getByText(/No text content block contains JSON matching structured content/)).toBeInTheDocument();
+    });
+
+    it("should handle empty text blocks gracefully", () => {
+      const toolResult = {
+        content: [
+          { type: "text", text: "" },
+          { type: "text", text: '{"result": "success"}' },
+        ],
+        structuredContent: { result: "success" },
+      };
+
+      render(<ToolResults toolResult={toolResult} selectedTool={mockTool} />);
+
+      expect(screen.getByText(/Found matching JSON content.*among multiple text blocks/)).toBeInTheDocument();
+    });
+
+    it("should not show compatibility check when tool has no output schema", () => {
+      const toolWithoutSchema: Tool = {
+        name: "noSchemaTool",
+        description: "Tool without schema",
+        inputSchema: {
+          type: "object",
+          properties: {},
+        },
+      };
+
+      const toolResult = {
+        content: [{ type: "text", text: '{"any": "data"}' }],
+        structuredContent: { any: "data" },
+      };
+
+      render(<ToolResults toolResult={toolResult} selectedTool={toolWithoutSchema} />);
+
+      // Should not show any compatibility messages
+      expect(screen.queryByText(/Found matching JSON content/)).not.toBeInTheDocument();
+      expect(screen.queryByText(/No text content blocks found/)).not.toBeInTheDocument();
+      expect(screen.queryByText(/No text content block contains JSON/)).not.toBeInTheDocument();
+    });
+  });
+
+  describe("Structured Content Validation", () => {
+    it("should show validation success for valid structured content", () => {
+      const toolResult = {
+        content: [],
+        structuredContent: { result: "success" },
+      };
+
+      render(<ToolResults toolResult={toolResult} selectedTool={mockTool} />);
+
+      expect(screen.getByText(/Valid according to output schema/)).toBeInTheDocument();
+    });
+
+    it("should show validation error for invalid structured content", () => {
+      const toolResult = {
+        content: [],
+        structuredContent: { result: 123 }, // Should be string
+      };
+
+      render(<ToolResults toolResult={toolResult} selectedTool={mockTool} />);
+
+      expect(screen.getByText(/Validation Error:/)).toBeInTheDocument();
+    });
+
+    it("should show error when structured content is missing for tool with output schema", () => {
+      const toolResult = {
+        content: [{ type: "text", text: "Some result" }],
+        // No structuredContent
+      };
+
+      render(<ToolResults toolResult={toolResult} selectedTool={mockTool} />);
+
+      expect(screen.getByText(/Tool has an output schema but did not return structured content/)).toBeInTheDocument();
+    });
+  });
+});
\ No newline at end of file
diff --git a/client/src/components/__tests__/ToolsTab.test.tsx b/client/src/components/__tests__/ToolsTab.test.tsx
index dc353ba5..bf8b1294 100644
--- a/client/src/components/__tests__/ToolsTab.test.tsx
+++ b/client/src/components/__tests__/ToolsTab.test.tsx
@@ -357,7 +357,104 @@ describe("ToolsTab", () => {
       // Should show compatibility result
       expect(
         screen.getByText(
-          /matches structured content|not a single text block|not valid JSON|does not match/,
+          /Found matching JSON content/,
+        ),
+      ).toBeInTheDocument();
+    });
+
+    it("should accept multiple content blocks with structured output", () => {
+      cacheToolOutputSchemas([toolWithOutputSchema]);
+
+      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({
+        selectedTool: toolWithOutputSchema,
+        toolResult: multipleBlocksResult,
+      });
+
+      // Should show compatible result with multiple blocks
+      expect(
+        screen.getByText(
+          /Found matching JSON content.*among multiple text blocks/,
+        ),
+      ).toBeInTheDocument();
+    });
+
+    it("should accept mixed content types with structured output", () => {
+      cacheToolOutputSchemas([toolWithOutputSchema]);
+
+      const mixedContentResult = {
+        content: [
+          { type: "text", text: "Weather report:" },
+          { type: "text", text: '{"temperature": 25}' },
+          { type: "image", data: "base64data", mimeType: "image/png" },
+        ],
+        structuredContent: { temperature: 25 },
+      };
+
+      renderToolsTab({
+        selectedTool: toolWithOutputSchema,
+        toolResult: mixedContentResult,
+      });
+
+      // Should show compatible result with additional content blocks
+      expect(
+        screen.getByText(
+          /Found matching JSON content.*with additional content blocks/,
+        ),
+      ).toBeInTheDocument();
+    });
+
+    it("should reject when no text blocks match structured content", () => {
+      cacheToolOutputSchemas([toolWithOutputSchema]);
+
+      const noMatchResult = {
+        content: [
+          { type: "text", text: "Some text" },
+          { type: "text", text: '{"humidity": 60}' }, // Different structure
+        ],
+        structuredContent: { temperature: 25 },
+      };
+
+      renderToolsTab({
+        selectedTool: toolWithOutputSchema,
+        toolResult: noMatchResult,
+      });
+
+      // Should show incompatible result
+      expect(
+        screen.getByText(
+          /No text content block contains JSON matching structured content/,
+        ),
+      ).toBeInTheDocument();
+    });
+
+    it("should reject when no text blocks are present", () => {
+      cacheToolOutputSchemas([toolWithOutputSchema]);
+
+      const noTextBlocksResult = {
+        content: [
+          { type: "image", data: "base64data", mimeType: "image/png" },
+        ],
+        structuredContent: { temperature: 25 },
+      };
+
+      renderToolsTab({
+        selectedTool: toolWithOutputSchema,
+        toolResult: noTextBlocksResult,
+      });
+
+      // Should show incompatible result
+      expect(
+        screen.getByText(
+          /No text content blocks found to match structured content/,
         ),
       ).toBeInTheDocument();
     });
@@ -376,7 +473,7 @@ 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/,
+          /Found matching JSON content|No text content blocks found|No text content block contains JSON/,
         ),
       ).not.toBeInTheDocument();
     });