diff --git a/src/core/task/Task.ts b/src/core/task/Task.ts
index c5be865731a..cf16df8dcc7 100644
--- a/src/core/task/Task.ts
+++ b/src/core/task/Task.ts
@@ -845,9 +845,19 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 			const message = this.messageQueueService.dequeueMessage()
 
 			if (message) {
-				setTimeout(async () => {
-					await this.submitUserMessage(message.text, message.images)
-				}, 0)
+				// Check if this is a tool approval ask that needs to be handled
+				if (
+					type === "tool" ||
+					type === "command" ||
+					type === "browser_action_launch" ||
+					type === "use_mcp_server"
+				) {
+					// For tool approvals, we need to approve first, then send the message if there's text/images
+					this.handleWebviewAskResponse("yesButtonClicked", message.text, message.images)
+				} else {
+					// For other ask types (like followup), fulfill the ask directly
+					this.setMessageResponse(message.text, message.images)
+				}
 			}
 		}
 
@@ -2898,4 +2908,28 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 	public get cwd() {
 		return this.workspacePath
 	}
+
+	/**
+	 * Process any queued messages by dequeuing and submitting them.
+	 * This ensures that queued user messages are sent when appropriate,
+	 * preventing them from getting stuck in the queue.
+	 *
+	 * @param context - Context string for logging (e.g., the calling tool name)
+	 */
+	public processQueuedMessages(): void {
+		try {
+			if (!this.messageQueueService.isEmpty()) {
+				const queued = this.messageQueueService.dequeueMessage()
+				if (queued) {
+					setTimeout(() => {
+						this.submitUserMessage(queued.text, queued.images).catch((err) =>
+							console.error(`[Task] Failed to submit queued message:`, err),
+						)
+					}, 0)
+				}
+			}
+		} catch (e) {
+			console.error(`[Task] Queue processing error:`, e)
+		}
+	}
 }
diff --git a/src/core/tools/__tests__/applyDiffTool.experiment.spec.ts b/src/core/tools/__tests__/applyDiffTool.experiment.spec.ts
index e763125d4a4..f82d4b1820c 100644
--- a/src/core/tools/__tests__/applyDiffTool.experiment.spec.ts
+++ b/src/core/tools/__tests__/applyDiffTool.experiment.spec.ts
@@ -40,6 +40,7 @@ describe("applyDiffTool experiment routing", () => {
 			api: {
 				getModel: vi.fn().mockReturnValue({ id: "test-model" }),
 			},
+			processQueuedMessages: vi.fn(),
 		} as any
 
 		mockBlock = {
diff --git a/src/core/tools/__tests__/multiApplyDiffTool.spec.ts b/src/core/tools/__tests__/multiApplyDiffTool.spec.ts
index 0bdedb9cd56..5e591f9fe79 100644
--- a/src/core/tools/__tests__/multiApplyDiffTool.spec.ts
+++ b/src/core/tools/__tests__/multiApplyDiffTool.spec.ts
@@ -91,6 +91,7 @@ describe("multiApplyDiffTool", () => {
 				trackFileContext: vi.fn().mockResolvedValue(undefined),
 			},
 			didEditFile: false,
+			processQueuedMessages: vi.fn(),
 		} as any
 
 		mockAskApproval = vi.fn().mockResolvedValue(true)
diff --git a/src/core/tools/applyDiffTool.ts b/src/core/tools/applyDiffTool.ts
index 903e3c846ec..dcdd1346240 100644
--- a/src/core/tools/applyDiffTool.ts
+++ b/src/core/tools/applyDiffTool.ts
@@ -207,6 +207,7 @@ export async function applyDiffToolLegacy(
 
 				if (!didApprove) {
 					await cline.diffViewProvider.revertChanges() // Cline likely handles closing the diff view
+					cline.processQueuedMessages()
 					return
 				}
 
@@ -245,11 +246,15 @@ export async function applyDiffToolLegacy(
 
 			await cline.diffViewProvider.reset()
 
+			// Process any queued messages after file edit completes
+			cline.processQueuedMessages()
+
 			return
 		}
 	} catch (error) {
 		await handleError("applying diff", error)
 		await cline.diffViewProvider.reset()
+		cline.processQueuedMessages()
 		return
 	}
 }
diff --git a/src/core/tools/insertContentTool.ts b/src/core/tools/insertContentTool.ts
index e22a3681671..e7d3a06ab92 100644
--- a/src/core/tools/insertContentTool.ts
+++ b/src/core/tools/insertContentTool.ts
@@ -187,6 +187,9 @@ export async function insertContentTool(
 		pushToolResult(message)
 
 		await cline.diffViewProvider.reset()
+
+		// Process any queued messages after file edit completes
+		cline.processQueuedMessages()
 	} catch (error) {
 		handleError("insert content", error)
 		await cline.diffViewProvider.reset()
diff --git a/src/core/tools/multiApplyDiffTool.ts b/src/core/tools/multiApplyDiffTool.ts
index 50695b1da73..d0fe6557503 100644
--- a/src/core/tools/multiApplyDiffTool.ts
+++ b/src/core/tools/multiApplyDiffTool.ts
@@ -172,6 +172,7 @@ Original error: ${errorMessage}`
 			TelemetryService.instance.captureDiffApplicationError(cline.taskId, cline.consecutiveMistakeCount)
 			await cline.say("diff_error", `Failed to parse apply_diff XML: ${errorMessage}`)
 			pushToolResult(detailedError)
+			cline.processQueuedMessages()
 			return
 		}
 	} else if (legacyPath && typeof legacyDiffContent === "string") {
@@ -195,6 +196,7 @@ Original error: ${errorMessage}`
 			"args (or legacy 'path' and 'diff' parameters)",
 		)
 		pushToolResult(errorMsg)
+		cline.processQueuedMessages()
 		return
 	}
 
@@ -210,6 +212,7 @@ Original error: ${errorMessage}`
 					: "args (must contain at least one valid file element)",
 			),
 		)
+		cline.processQueuedMessages()
 		return
 	}
 
@@ -675,10 +678,12 @@ ${errorDetails ? `\nTechnical details:\n${errorDetails}\n` : ""}
 
 		// Push the final result combining all operation results
 		pushToolResult(results.join("\n\n") + singleBlockNotice)
+		cline.processQueuedMessages()
 		return
 	} catch (error) {
 		await handleError("applying diff", error)
 		await cline.diffViewProvider.reset()
+		cline.processQueuedMessages()
 		return
 	}
 }
diff --git a/src/core/tools/searchAndReplaceTool.ts b/src/core/tools/searchAndReplaceTool.ts
index 49129344158..b0ee3947e1e 100644
--- a/src/core/tools/searchAndReplaceTool.ts
+++ b/src/core/tools/searchAndReplaceTool.ts
@@ -263,6 +263,9 @@ export async function searchAndReplaceTool(
 		// Record successful tool usage and cleanup
 		cline.recordToolUsage("search_and_replace")
 		await cline.diffViewProvider.reset()
+
+		// Process any queued messages after file edit completes
+		cline.processQueuedMessages()
 	} catch (error) {
 		handleError("search and replace", error)
 		await cline.diffViewProvider.reset()
diff --git a/src/core/tools/writeToFileTool.ts b/src/core/tools/writeToFileTool.ts
index e82eab92bc8..5abd96a20af 100644
--- a/src/core/tools/writeToFileTool.ts
+++ b/src/core/tools/writeToFileTool.ts
@@ -308,6 +308,9 @@ export async function writeToFileTool(
 
 			await cline.diffViewProvider.reset()
 
+			// Process any queued messages after file edit completes
+			cline.processQueuedMessages()
+
 			return
 		}
 	} catch (error) {