diff --git a/src/core/diff/strategies/__tests__/grok-malformed-diff.spec.ts b/src/core/diff/strategies/__tests__/grok-malformed-diff.spec.ts
new file mode 100644
index 0000000000..774fdf8266
--- /dev/null
+++ b/src/core/diff/strategies/__tests__/grok-malformed-diff.spec.ts
@@ -0,0 +1,327 @@
+import { MultiSearchReplaceDiffStrategy } from "../multi-search-replace"
+import { MultiFileSearchReplaceDiffStrategy } from "../multi-file-search-replace"
+
+describe("Grok Malformed Diff Detection", () => {
+	describe("MultiSearchReplaceDiffStrategy", () => {
+		let strategy: MultiSearchReplaceDiffStrategy
+
+		beforeEach(() => {
+			strategy = new MultiSearchReplaceDiffStrategy()
+		})
+
+		describe("detectGrokMalformedDiff", () => {
+			it("detects consecutive separators", () => {
+				const diff = "<<<<<<< SEARCH\ncontent\n=======\n=======\n>>>>>>> REPLACE"
+				const result = strategy["detectGrokMalformedDiff"](diff)
+				expect(result).toBe(true)
+			})
+
+			it("detects separator before search marker", () => {
+				const diff = "=======\n<<<<<<< SEARCH\ncontent\n>>>>>>> REPLACE"
+				const result = strategy["detectGrokMalformedDiff"](diff)
+				expect(result).toBe(true)
+			})
+
+			it("detects too many separators", () => {
+				const diff = "<<<<<<< SEARCH\ncontent\n=======\n=======\n=======\n>>>>>>> REPLACE"
+				const result = strategy["detectGrokMalformedDiff"](diff)
+				expect(result).toBe(true)
+			})
+
+			it("returns false for valid diff", () => {
+				const diff = "<<<<<<< SEARCH\ncontent\n=======\nreplacement\n>>>>>>> REPLACE"
+				const result = strategy["detectGrokMalformedDiff"](diff)
+				expect(result).toBe(false)
+			})
+
+			it("returns false for multiple valid diffs", () => {
+				const diff =
+					"<<<<<<< SEARCH\ncontent1\n=======\nreplace1\n>>>>>>> REPLACE\n\n" +
+					"<<<<<<< SEARCH\ncontent2\n=======\nreplace2\n>>>>>>> REPLACE"
+				const result = strategy["detectGrokMalformedDiff"](diff)
+				expect(result).toBe(false)
+			})
+		})
+
+		describe("analyzeDiffStructure", () => {
+			it("provides debugging info for malformed diff", () => {
+				const diff = "<<<<<<< SEARCH\ncontent\n=======\n=======\n>>>>>>> REPLACE"
+				const result = strategy["analyzeDiffStructure"](diff)
+
+				expect(result).toContain("Found 1 SEARCH markers")
+				expect(result).toContain("Found 2 separator (=======) markers")
+				expect(result).toContain("Found 1 REPLACE markers")
+				expect(result).toContain("WARNING: More separators than SEARCH blocks")
+				expect(result).toContain("ERROR: Consecutive separators")
+			})
+
+			it("provides debugging info for unbalanced markers", () => {
+				const diff = "<<<<<<< SEARCH\ncontent\n=======\nreplace\n<<<<<<< SEARCH\nanother"
+				const result = strategy["analyzeDiffStructure"](diff)
+
+				expect(result).toContain("Found 2 SEARCH markers")
+				expect(result).toContain("Found 1 separator (=======) markers")
+				expect(result).toContain("Found 0 REPLACE markers")
+				expect(result).toContain("WARNING: Unbalanced markers")
+			})
+		})
+
+		describe("validateMarkerSequencing with Grok detection", () => {
+			it("returns helpful error for Grok-style malformed diff", () => {
+				const diff = "=======\ncontent\n>>>>>>> REPLACE"
+				const result = strategy["validateMarkerSequencing"](diff)
+
+				expect(result.success).toBe(false)
+				expect(result.error).toContain("The diff content appears to be malformed")
+				expect(result.error).toContain("This often happens when AI models generate incorrect diff syntax")
+				expect(result.error).toContain("DEBUGGING INFO:")
+				expect(result.error).toContain("SUGGESTIONS:")
+				expect(result.debugInfo).toBeDefined()
+			})
+
+			it("returns helpful error for consecutive separators", () => {
+				const diff = "<<<<<<< SEARCH\ncontent\n=======\n=======\n>>>>>>> REPLACE"
+				const result = strategy["validateMarkerSequencing"](diff)
+
+				expect(result.success).toBe(false)
+				expect(result.error).toContain("The diff content appears to be malformed")
+				expect(result.error).toContain("Try using the read_file tool first")
+				expect(result.error).toContain("Use simpler, smaller diff blocks")
+			})
+
+			it("still validates normal diffs correctly", () => {
+				const diff = "<<<<<<< SEARCH\ncontent\n=======\nreplacement\n>>>>>>> REPLACE"
+				const result = strategy["validateMarkerSequencing"](diff)
+
+				expect(result.success).toBe(true)
+			})
+		})
+
+		describe("applyDiff with malformed content", () => {
+			it("returns error with debug info for malformed diff", async () => {
+				const originalContent = "function test() {\n  return true;\n}"
+				const malformedDiff = "=======\nfunction test() {\n  return false;\n}\n>>>>>>> REPLACE"
+
+				const result = await strategy.applyDiff(originalContent, malformedDiff)
+
+				expect(result.success).toBe(false)
+				if (!result.success) {
+					expect(result.error).toContain("The diff content appears to be malformed")
+				}
+			})
+
+			it("handles Grok-style issues gracefully", async () => {
+				const originalContent = "const x = 1;"
+				const grokDiff = "<<<<<<< SEARCH\nconst x = 1;\n=======\n=======\nconst x = 2;\n>>>>>>> REPLACE"
+
+				const result = await strategy.applyDiff(originalContent, grokDiff)
+
+				expect(result.success).toBe(false)
+				if (!result.success) {
+					expect(result.error).toContain("The diff content appears to be malformed")
+					expect(result.error).toContain("ERROR: Consecutive separators")
+				}
+			})
+		})
+	})
+
+	describe("MultiFileSearchReplaceDiffStrategy", () => {
+		let strategy: MultiFileSearchReplaceDiffStrategy
+
+		beforeEach(() => {
+			strategy = new MultiFileSearchReplaceDiffStrategy()
+		})
+
+		describe("detectGrokMalformedDiff", () => {
+			it("detects consecutive separators", () => {
+				const diff = "<<<<<<< SEARCH\ncontent\n=======\n=======\n>>>>>>> REPLACE"
+				const result = strategy["detectGrokMalformedDiff"](diff)
+				expect(result).toBe(true)
+			})
+
+			it("detects separator before search marker", () => {
+				const diff = "=======\n<<<<<<< SEARCH\ncontent\n>>>>>>> REPLACE"
+				const result = strategy["detectGrokMalformedDiff"](diff)
+				expect(result).toBe(true)
+			})
+
+			it("detects too many separators", () => {
+				const diff = "<<<<<<< SEARCH\ncontent\n=======\n=======\n=======\n>>>>>>> REPLACE"
+				const result = strategy["detectGrokMalformedDiff"](diff)
+				expect(result).toBe(true)
+			})
+
+			it("returns false for valid diff", () => {
+				const diff = "<<<<<<< SEARCH\ncontent\n=======\nreplacement\n>>>>>>> REPLACE"
+				const result = strategy["detectGrokMalformedDiff"](diff)
+				expect(result).toBe(false)
+			})
+
+			it("returns false for multiple valid diffs", () => {
+				const diff =
+					"<<<<<<< SEARCH\ncontent1\n=======\nreplace1\n>>>>>>> REPLACE\n\n" +
+					"<<<<<<< SEARCH\ncontent2\n=======\nreplace2\n>>>>>>> REPLACE"
+				const result = strategy["detectGrokMalformedDiff"](diff)
+				expect(result).toBe(false)
+			})
+		})
+
+		describe("analyzeDiffStructure", () => {
+			it("provides debugging info for malformed diff", () => {
+				const diff = "<<<<<<< SEARCH\ncontent\n=======\n=======\n>>>>>>> REPLACE"
+				const result = strategy["analyzeDiffStructure"](diff)
+
+				expect(result).toContain("Found 1 SEARCH markers")
+				expect(result).toContain("Found 2 separator (=======) markers")
+				expect(result).toContain("Found 1 REPLACE markers")
+				expect(result).toContain("WARNING: More separators than SEARCH blocks")
+				expect(result).toContain("ERROR: Consecutive separators")
+			})
+
+			it("provides debugging info for unbalanced markers", () => {
+				const diff = "<<<<<<< SEARCH\ncontent\n=======\nreplace\n<<<<<<< SEARCH\nanother"
+				const result = strategy["analyzeDiffStructure"](diff)
+
+				expect(result).toContain("Found 2 SEARCH markers")
+				expect(result).toContain("Found 1 separator (=======) markers")
+				expect(result).toContain("Found 0 REPLACE markers")
+				expect(result).toContain("WARNING: Unbalanced markers")
+			})
+		})
+
+		describe("validateMarkerSequencing with Grok detection", () => {
+			it("returns helpful error for Grok-style malformed diff", () => {
+				const diff = "=======\ncontent\n>>>>>>> REPLACE"
+				const result = strategy["validateMarkerSequencing"](diff)
+
+				expect(result.success).toBe(false)
+				expect(result.error).toContain("The diff content appears to be malformed")
+				expect(result.error).toContain("This often happens when AI models generate incorrect diff syntax")
+				expect(result.error).toContain("DEBUGGING INFO:")
+				expect(result.error).toContain("SUGGESTIONS:")
+				expect(result.debugInfo).toBeDefined()
+			})
+
+			it("returns helpful error for consecutive separators", () => {
+				const diff = "<<<<<<< SEARCH\ncontent\n=======\n=======\n>>>>>>> REPLACE"
+				const result = strategy["validateMarkerSequencing"](diff)
+
+				expect(result.success).toBe(false)
+				expect(result.error).toContain("The diff content appears to be malformed")
+				expect(result.error).toContain("Try using the read_file tool first")
+				expect(result.error).toContain("Use simpler, smaller diff blocks")
+			})
+
+			it("still validates normal diffs correctly", () => {
+				const diff = "<<<<<<< SEARCH\ncontent\n=======\nreplacement\n>>>>>>> REPLACE"
+				const result = strategy["validateMarkerSequencing"](diff)
+
+				expect(result.success).toBe(true)
+			})
+		})
+
+		describe("applyDiff with malformed content", () => {
+			it("returns error with debug info for malformed diff", async () => {
+				const originalContent = "function test() {\n  return true;\n}"
+				const malformedDiff = "=======\nfunction test() {\n  return false;\n}\n>>>>>>> REPLACE"
+
+				const result = await strategy.applyDiff(originalContent, malformedDiff)
+
+				expect(result.success).toBe(false)
+				if (!result.success) {
+					expect(result.error).toContain("The diff content appears to be malformed")
+				}
+			})
+
+			it("handles Grok-style issues gracefully", async () => {
+				const originalContent = "const x = 1;"
+				const grokDiff = "<<<<<<< SEARCH\nconst x = 1;\n=======\n=======\nconst x = 2;\n>>>>>>> REPLACE"
+
+				const result = await strategy.applyDiff(originalContent, grokDiff)
+
+				expect(result.success).toBe(false)
+				if (!result.success) {
+					expect(result.error).toContain("The diff content appears to be malformed")
+					expect(result.error).toContain("ERROR: Consecutive separators")
+				}
+			})
+		})
+	})
+
+	describe("Real-world Grok scenarios", () => {
+		let strategy: MultiSearchReplaceDiffStrategy
+
+		beforeEach(() => {
+			strategy = new MultiSearchReplaceDiffStrategy()
+		})
+
+		it("handles case where Grok adds consecutive separators", async () => {
+			const originalContent = `function processPayment(amount) {
+    // Process payment logic
+    return { success: true };
+}`
+
+			// Simulating a Grok model that incorrectly adds consecutive separators
+			// This triggers Grok detection
+			const grokDiff = [
+				"<<<<<<< SEARCH",
+				"function processPayment(amount) {",
+				"    // Process payment logic",
+				"=======",
+				"=======",
+				"function processPayment(amount, currency) {",
+				"    // Enhanced payment logic",
+				">>>>>>> REPLACE",
+			].join("\n")
+
+			const result = await strategy.applyDiff(originalContent, grokDiff)
+
+			expect(result.success).toBe(false)
+			if (!result.success) {
+				expect(result.error).toContain("The diff content appears to be malformed")
+			}
+		})
+
+		it("handles case where separator appears before search marker", async () => {
+			// This simulates the exact issue @mrbm reported
+			const originalContent = `export function calculateTotal(items) {
+    let total = 0;
+    for (const item of items) {
+        total += item.price;
+    }
+    return total;
+}`
+
+			// Malformed diff that Grok might generate - separator before search
+			const malformedDiff = [
+				"=======",
+				"<<<<<<< SEARCH",
+				"export function calculateTotal(items) {",
+				"    let total = 0;",
+				"=======",
+				"export function calculateTotal(items, taxRate = 0) {",
+				"    let total = 0;",
+				">>>>>>> REPLACE",
+			].join("\n")
+
+			const result = await strategy.applyDiff(originalContent, malformedDiff)
+
+			expect(result.success).toBe(false)
+			if (!result.success) {
+				expect(result.error).toContain("The diff content appears to be malformed")
+				expect(result.error).not.toContain("When removing merge conflict markers")
+				expect(result.error).toContain("AI models generate incorrect diff syntax")
+			}
+		})
+
+		it("provides actionable suggestions for Grok users", () => {
+			const diff = "=======\ncontent\n>>>>>>> REPLACE"
+			const result = strategy["validateMarkerSequencing"](diff)
+
+			expect(result.error).toContain("Try using the read_file tool first")
+			expect(result.error).toContain("Ensure your SEARCH block exactly matches")
+			expect(result.error).toContain("Use simpler, smaller diff blocks")
+			expect(result.error).toContain("CORRECT FORMAT:")
+		})
+	})
+})
diff --git a/src/core/diff/strategies/__tests__/multi-search-replace.spec.ts b/src/core/diff/strategies/__tests__/multi-search-replace.spec.ts
index b25286f5fa..ebe78ade4e 100644
--- a/src/core/diff/strategies/__tests__/multi-search-replace.spec.ts
+++ b/src/core/diff/strategies/__tests__/multi-search-replace.spec.ts
@@ -96,8 +96,9 @@ describe("MultiSearchReplaceDiffStrategy", () => {
 			const diff = "=======\n" + "content\n" + ">>>>>>> REPLACE"
 			const result = strategy["validateMarkerSequencing"](diff)
 			expect(result.success).toBe(false)
-			expect(result.error).toContain("'=======' found in your diff content")
-			expect(result.error).toContain("Diff block is malformed")
+			// This now triggers Grok detection instead of the regular error
+			expect(result.error).toContain("The diff content appears to be malformed")
+			expect(result.error).toContain("AI models generate incorrect diff syntax")
 		})
 
 		it("detects missing separator", () => {
@@ -112,8 +113,9 @@ describe("MultiSearchReplaceDiffStrategy", () => {
 			const diff = "<<<<<<< SEARCH\n" + "content\n" + "=======\n" + "=======\n" + ">>>>>>> REPLACE"
 			const result = strategy["validateMarkerSequencing"](diff)
 			expect(result.success).toBe(false)
-			expect(result.error).toContain("'=======' found in your diff content")
-			expect(result.error).toContain("When removing merge conflict markers")
+			// This now triggers Grok detection for consecutive separators
+			expect(result.error).toContain("The diff content appears to be malformed")
+			expect(result.error).toContain("AI models generate incorrect diff syntax")
 		})
 
 		it("detects replace before separator (merge conflict message)", () => {
diff --git a/src/core/diff/strategies/multi-file-search-replace.ts b/src/core/diff/strategies/multi-file-search-replace.ts
index a212cf2b8e..417c7a33da 100644
--- a/src/core/diff/strategies/multi-file-search-replace.ts
+++ b/src/core/diff/strategies/multi-file-search-replace.ts
@@ -242,7 +242,36 @@ Each file requires its own path, start_line, and diff elements.
 			.replace(/^\\:start_line:/gm, ":start_line:")
 	}
 
-	private validateMarkerSequencing(diffContent: string): { success: boolean; error?: string } {
+	private validateMarkerSequencing(diffContent: string): { success: boolean; error?: string; debugInfo?: string } {
+		// First, check if this looks like a Grok model issue with malformed content
+		// Grok models sometimes generate extra markers or malformed diffs
+		const isLikelyGrokIssue = this.detectGrokMalformedDiff(diffContent)
+
+		if (isLikelyGrokIssue) {
+			// Log for debugging but try to be more helpful
+			const debugInfo = this.analyzeDiffStructure(diffContent)
+			return {
+				success: false,
+				error:
+					`ERROR: The diff content appears to be malformed. This often happens when AI models generate incorrect diff syntax.\n\n` +
+					`DEBUGGING INFO:\n${debugInfo}\n\n` +
+					`SUGGESTIONS:\n` +
+					`1. Try using the read_file tool first to see the exact file content\n` +
+					`2. Ensure your SEARCH block exactly matches the file content (including whitespace)\n` +
+					`3. Use simpler, smaller diff blocks for more reliable results\n` +
+					`4. If the file contains special characters or markers, they may need escaping\n\n` +
+					`CORRECT FORMAT:\n` +
+					`<<<<<<< SEARCH\n` +
+					`:start_line: (optional) The line number where search starts\n` +
+					`-------\n` +
+					`[exact content to find]\n` +
+					`=======\n` +
+					`[new content to replace with]\n` +
+					`>>>>>>> REPLACE`,
+				debugInfo: debugInfo,
+			}
+		}
+
 		enum State {
 			START,
 			AFTER_SEARCH,
@@ -291,7 +320,7 @@ Each file requires its own path, start_line, and diff elements.
 				"\n" +
 				"CORRECT FORMAT:\n\n" +
 				"<<<<<<< SEARCH\n" +
-				":start_line: (required) The line number of original content where the search block starts.\n" +
+				":start_line: (optional) The line number where search starts\n" +
 				"-------\n" +
 				"[exact content to find including whitespace]\n" +
 				"=======\n" +
@@ -387,6 +416,83 @@ Each file requires its own path, start_line, and diff elements.
 				}
 	}
 
+	/**
+	 * Detects if the diff content appears to be malformed in a way typical of Grok models
+	 */
+	private detectGrokMalformedDiff(diffContent: string): boolean {
+		const lines = diffContent.split("\n")
+
+		// Check for common Grok model issues:
+		// 1. Multiple consecutive separators
+		// 2. Separators appearing before any SEARCH marker
+		// 3. Incomplete diff blocks
+		// 4. Markers in unexpected positions
+
+		let consecutiveSeparators = 0
+		let hasSearchMarker = false
+		let separatorBeforeSearch = false
+
+		for (let i = 0; i < lines.length; i++) {
+			const line = lines[i].trim()
+
+			if (line === "=======") {
+				if (!hasSearchMarker) {
+					separatorBeforeSearch = true
+				}
+				if (i > 0 && lines[i - 1].trim() === "=======") {
+					consecutiveSeparators++
+				}
+			}
+
+			if (line.startsWith("<<<<<<< SEARCH")) {
+				hasSearchMarker = true
+			}
+		}
+
+		// If we see patterns typical of Grok issues, flag it
+		return (
+			consecutiveSeparators > 0 ||
+			separatorBeforeSearch ||
+			lines.filter((l) => l.trim() === "=======").length >
+				lines.filter((l) => l.trim().startsWith("<<<<<<< SEARCH")).length * 2
+		)
+	}
+
+	/**
+	 * Analyzes the diff structure to provide debugging information
+	 */
+	private analyzeDiffStructure(diffContent: string): string {
+		const lines = diffContent.split("\n")
+		const searchMarkers = lines.filter((l) => l.trim().startsWith("<<<<<<< SEARCH")).length
+		const separators = lines.filter((l) => l.trim() === "=======").length
+		const replaceMarkers = lines.filter((l) => l.trim() === ">>>>>>> REPLACE").length
+
+		let debugInfo = `- Found ${searchMarkers} SEARCH markers\n`
+		debugInfo += `- Found ${separators} separator (=======) markers\n`
+		debugInfo += `- Found ${replaceMarkers} REPLACE markers\n`
+
+		// Check for balance
+		if (searchMarkers !== replaceMarkers) {
+			debugInfo += `- WARNING: Unbalanced markers (SEARCH: ${searchMarkers}, REPLACE: ${replaceMarkers})\n`
+		}
+		if (separators > searchMarkers) {
+			debugInfo += `- WARNING: More separators than SEARCH blocks (may indicate malformed content)\n`
+		}
+
+		// Find problematic lines
+		for (let i = 0; i < lines.length; i++) {
+			const line = lines[i]
+			if (line.trim() === "=======" && i > 0) {
+				const prevLine = lines[i - 1].trim()
+				if (prevLine === "=======") {
+					debugInfo += `- ERROR: Consecutive separators at lines ${i} and ${i + 1}\n`
+				}
+			}
+		}
+
+		return debugInfo
+	}
+
 	async applyDiff(
 		originalContent: string,
 		diffContent: string | Array<{ content: string; startLine?: number }>,
diff --git a/src/core/diff/strategies/multi-search-replace.ts b/src/core/diff/strategies/multi-search-replace.ts
index a6a9913203..c29aaf1e2a 100644
--- a/src/core/diff/strategies/multi-search-replace.ts
+++ b/src/core/diff/strategies/multi-search-replace.ts
@@ -190,7 +190,36 @@ Only use a single line of '=======' between search and replacement content, beca
 			.replace(/^\\:start_line:/gm, ":start_line:")
 	}
 
-	private validateMarkerSequencing(diffContent: string): { success: boolean; error?: string } {
+	private validateMarkerSequencing(diffContent: string): { success: boolean; error?: string; debugInfo?: string } {
+		// First, check if this looks like a Grok model issue with malformed content
+		// Grok models sometimes generate extra markers or malformed diffs
+		const isLikelyGrokIssue = this.detectGrokMalformedDiff(diffContent)
+
+		if (isLikelyGrokIssue) {
+			// Log for debugging but try to be more helpful
+			const debugInfo = this.analyzeDiffStructure(diffContent)
+			return {
+				success: false,
+				error:
+					`ERROR: The diff content appears to be malformed. This often happens when AI models generate incorrect diff syntax.\n\n` +
+					`DEBUGGING INFO:\n${debugInfo}\n\n` +
+					`SUGGESTIONS:\n` +
+					`1. Try using the read_file tool first to see the exact file content\n` +
+					`2. Ensure your SEARCH block exactly matches the file content (including whitespace)\n` +
+					`3. Use simpler, smaller diff blocks for more reliable results\n` +
+					`4. If the file contains special characters or markers, they may need escaping\n\n` +
+					`CORRECT FORMAT:\n` +
+					`<<<<<<< SEARCH\n` +
+					`:start_line: (optional) The line number where search starts\n` +
+					`-------\n` +
+					`[exact content to find]\n` +
+					`=======\n` +
+					`[new content to replace with]\n` +
+					`>>>>>>> REPLACE`,
+				debugInfo: debugInfo,
+			}
+		}
+
 		enum State {
 			START,
 			AFTER_SEARCH,
@@ -238,7 +267,7 @@ Only use a single line of '=======' between search and replacement content, beca
 				"\n" +
 				"CORRECT FORMAT:\n\n" +
 				"<<<<<<< SEARCH\n" +
-				":start_line: (required) The line number of original content where the search block starts.\n" +
+				":start_line: (optional) The line number where search starts\n" +
 				"-------\n" +
 				"[exact content to find including whitespace]\n" +
 				"=======\n" +
@@ -334,6 +363,83 @@ Only use a single line of '=======' between search and replacement content, beca
 				}
 	}
 
+	/**
+	 * Detects if the diff content appears to be malformed in a way typical of Grok models
+	 */
+	private detectGrokMalformedDiff(diffContent: string): boolean {
+		const lines = diffContent.split("\n")
+
+		// Check for common Grok model issues:
+		// 1. Multiple consecutive separators
+		// 2. Separators appearing before any SEARCH marker
+		// 3. Incomplete diff blocks
+		// 4. Markers in unexpected positions
+
+		let consecutiveSeparators = 0
+		let hasSearchMarker = false
+		let separatorBeforeSearch = false
+
+		for (let i = 0; i < lines.length; i++) {
+			const line = lines[i].trim()
+
+			if (line === "=======") {
+				if (!hasSearchMarker) {
+					separatorBeforeSearch = true
+				}
+				if (i > 0 && lines[i - 1].trim() === "=======") {
+					consecutiveSeparators++
+				}
+			}
+
+			if (line.startsWith("<<<<<<< SEARCH")) {
+				hasSearchMarker = true
+			}
+		}
+
+		// If we see patterns typical of Grok issues, flag it
+		return (
+			consecutiveSeparators > 0 ||
+			separatorBeforeSearch ||
+			lines.filter((l) => l.trim() === "=======").length >
+				lines.filter((l) => l.trim().startsWith("<<<<<<< SEARCH")).length * 2
+		)
+	}
+
+	/**
+	 * Analyzes the diff structure to provide debugging information
+	 */
+	private analyzeDiffStructure(diffContent: string): string {
+		const lines = diffContent.split("\n")
+		const searchMarkers = lines.filter((l) => l.trim().startsWith("<<<<<<< SEARCH")).length
+		const separators = lines.filter((l) => l.trim() === "=======").length
+		const replaceMarkers = lines.filter((l) => l.trim() === ">>>>>>> REPLACE").length
+
+		let debugInfo = `- Found ${searchMarkers} SEARCH markers\n`
+		debugInfo += `- Found ${separators} separator (=======) markers\n`
+		debugInfo += `- Found ${replaceMarkers} REPLACE markers\n`
+
+		// Check for balance
+		if (searchMarkers !== replaceMarkers) {
+			debugInfo += `- WARNING: Unbalanced markers (SEARCH: ${searchMarkers}, REPLACE: ${replaceMarkers})\n`
+		}
+		if (separators > searchMarkers) {
+			debugInfo += `- WARNING: More separators than SEARCH blocks (may indicate malformed content)\n`
+		}
+
+		// Find problematic lines
+		for (let i = 0; i < lines.length; i++) {
+			const line = lines[i]
+			if (line.trim() === "=======" && i > 0) {
+				const prevLine = lines[i - 1].trim()
+				if (prevLine === "=======") {
+					debugInfo += `- ERROR: Consecutive separators at lines ${i} and ${i + 1}\n`
+				}
+			}
+		}
+
+		return debugInfo
+	}
+
 	async applyDiff(
 		originalContent: string,
 		diffContent: string,