diff --git a/src/core/webview/ClineProvider.ts b/src/core/webview/ClineProvider.ts
index fd70c41af09..f0359cd10d1 100644
--- a/src/core/webview/ClineProvider.ts
+++ b/src/core/webview/ClineProvider.ts
@@ -3245,23 +3245,58 @@ export class ClineProvider
 			initialStatus: "active",
 		})
 
-		// 5) Persist parent delegation metadata
-		try {
-			const { historyItem } = await this.getTaskWithId(parentTaskId)
-			const childIds = Array.from(new Set([...(historyItem.childIds ?? []), child.taskId]))
-			const updatedHistory: typeof historyItem = {
-				...historyItem,
-				status: "delegated",
-				delegatedToId: child.taskId,
-				awaitingChildId: child.taskId,
-				childIds,
+		// 5) Persist parent delegation metadata with retry logic
+		// This is critical - if it fails, the parent task can "disappear" from the UI
+		// or appear in an inconsistent state
+		const maxRetries = 3
+		let lastError: Error | undefined
+
+		for (let attempt = 1; attempt <= maxRetries; attempt++) {
+			try {
+				const { historyItem } = await this.getTaskWithId(parentTaskId)
+				const childIds = Array.from(new Set([...(historyItem.childIds ?? []), child.taskId]))
+				const updatedHistory: typeof historyItem = {
+					...historyItem,
+					status: "delegated",
+					delegatedToId: child.taskId,
+					awaitingChildId: child.taskId,
+					childIds,
+				}
+				await this.updateTaskHistory(updatedHistory)
+				lastError = undefined // Success - clear any previous error
+				break
+			} catch (err) {
+				lastError = err as Error
+				this.log(
+					`[delegateParentAndOpenChild] Attempt ${attempt}/${maxRetries} failed to persist parent metadata for ${parentTaskId} -> ${child.taskId}: ${
+						(err as Error)?.message ?? String(err)
+					}`,
+				)
+
+				// If this was the last attempt, we need to handle the failure more seriously
+				if (attempt === maxRetries) {
+					const errorMsg = `Failed to persist parent task delegation metadata after ${maxRetries} attempts. Parent task ${parentTaskId} may appear in an inconsistent state.`
+					this.log(`[delegateParentAndOpenChild] CRITICAL: ${errorMsg}`)
+					console.error(`[delegateParentAndOpenChild] CRITICAL:`, errorMsg, err)
+
+					// Show a user-visible warning for this critical failure
+					// Note: We don't throw here because the child task was already created
+					// and is now the active task. Throwing would leave both tasks in a bad state.
+					vscode.window.showWarningMessage(
+						`Warning: Task delegation succeeded but metadata persistence failed. The parent task may not resume correctly. Error: ${(err as Error)?.message ?? String(err)}`,
+					)
+				} else {
+					// Wait before retry with exponential backoff
+					await delay(100 * Math.pow(2, attempt - 1))
+				}
 			}
-			await this.updateTaskHistory(updatedHistory)
-		} catch (err) {
+		}
+
+		// If we failed all retries, log it clearly but don't throw
+		// (child task is already active and functional)
+		if (lastError) {
 			this.log(
-				`[delegateParentAndOpenChild] Failed to persist parent metadata for ${parentTaskId} -> ${child.taskId}: ${
-					(err as Error)?.message ?? String(err)
-				}`,
+				`[delegateParentAndOpenChild] WARNING: Proceeding with delegation despite metadata persistence failure. Parent=${parentTaskId}, Child=${child.taskId}`,
 			)
 		}
 
diff --git a/src/utils/safeWriteJson.ts b/src/utils/safeWriteJson.ts
index c32dd92ce5d..f9e462375c8 100644
--- a/src/utils/safeWriteJson.ts
+++ b/src/utils/safeWriteJson.ts
@@ -54,18 +54,18 @@ async function safeWriteJson(filePath: string, data: any, options?: SafeWriteJso
 	// Acquire the lock before any file operations
 	try {
 		releaseLock = await lockfile.lock(absoluteFilePath, {
-			stale: 31000, // Stale after 31 seconds
+			stale: 60000, // Increased to 60 seconds to handle complex orchestrator scenarios with multiple rapid writes
 			update: 10000, // Update mtime every 10 seconds to prevent staleness if operation is long
 			realpath: false, // the file may not exist yet, which is acceptable
 			retries: {
 				// Configuration for retrying lock acquisition
-				retries: 5, // Number of retries after the initial attempt
+				retries: 10, // Increased retries to handle rapid succession writes during orchestrator delegation
 				factor: 2, // Exponential backoff factor (e.g., 100ms, 200ms, 400ms, ...)
-				minTimeout: 100, // Minimum time to wait before the first retry (in ms)
-				maxTimeout: 1000, // Maximum time to wait for any single retry (in ms)
+				minTimeout: 200, // Increased minimum timeout for better contention handling
+				maxTimeout: 2000, // Increased maximum timeout for high-contention scenarios
 			},
 			onCompromised: (err) => {
-				console.error(`Lock at ${absoluteFilePath} was compromised:`, err)
+				console.error(`[safeWriteJson] Lock at ${absoluteFilePath} was compromised:`, err)
 				throw err
 			},
 		})
@@ -73,9 +73,22 @@ async function safeWriteJson(filePath: string, data: any, options?: SafeWriteJso
 		// If lock acquisition fails, we throw immediately.
 		// The releaseLock remains a no-op, so the finally block in the main file operations
 		// try-catch-finally won't try to release an unacquired lock if this path is taken.
-		console.error(`Failed to acquire lock for ${absoluteFilePath}:`, lockError)
-		// Propagate the lock acquisition error
-		throw lockError
+		console.error(
+			`[safeWriteJson] Failed to acquire lock for ${absoluteFilePath} after retries. This may indicate:
+- High contention from rapid task delegation (e.g., Orchestrator mode creating multiple subtasks)
+- A stale lock from a crashed process
+- File system issues
+
+Error:`,
+			lockError,
+		)
+		// Propagate the lock acquisition error with enhanced context
+		const enhancedError = new Error(
+			`Failed to acquire file lock for ${path.basename(absoluteFilePath)}: ${lockError instanceof Error ? lockError.message : String(lockError)}`,
+		)
+		;(enhancedError as any).originalError = lockError
+		;(enhancedError as any).filePath = absoluteFilePath
+		throw enhancedError
 	}
 
 	// Variables to hold the actual paths of temp files if they are created.