diff --git a/src/channel/guaranteedChannel.ts b/src/channel/guaranteedChannel.ts
index a2f264ca..a65b47e0 100644
--- a/src/channel/guaranteedChannel.ts
+++ b/src/channel/guaranteedChannel.ts
@@ -99,7 +99,7 @@ export class GuaranteedChannel<M, S> implements OutputChannel<M> {
                     () => {
                         if (this.closed) {
                             // Cancel delay immediately when the channel is closed
-                            abort(MessageDeliveryError.nonRetryable('Connection deliberately closed.'));
+                            abort(MessageDeliveryError.retryable('Connection deliberately closed.'));
                         }
                     },
                     0,
diff --git a/src/channel/queuedChannel.ts b/src/channel/queuedChannel.ts
index fd68a0d1..e87b718d 100644
--- a/src/channel/queuedChannel.ts
+++ b/src/channel/queuedChannel.ts
@@ -39,18 +39,10 @@ export class QueuedChannel<T> implements OutputChannel<T> {
         }
 
         if (this.pending === undefined) {
-            this.pending = this.queue.isEmpty()
-                ? Promise.resolve()
-                : Promise.reject(MessageDeliveryError.retryable('The queue must be flushed.'));
+            this.pending = this.requeue();
         }
 
-        this.enqueue(message);
-
-        this.pending = this.pending.then(
-            () => this.channel
-                .publish(message)
-                .then(this.dequeue.bind(this)),
-        );
+        this.pending = this.chainNext(this.pending, message, true);
 
         return this.pending;
     }
@@ -86,16 +78,55 @@ export class QueuedChannel<T> implements OutputChannel<T> {
         this.logger.debug(`Queue length: ${length}`);
 
         for (const message of this.queue.all()) {
-            this.pending = this.pending.then(
-                () => this.channel
-                    .publish(message)
-                    .then(this.dequeue.bind(this)),
-            );
+            this.pending = this.chainNext(this.pending, message);
         }
 
         return this.pending;
     }
 
+    private async chainNext(previous: Promise<void>, message: T, enqueue = false): Promise<void> {
+        if (enqueue) {
+            this.enqueue(message);
+        }
+
+        try {
+            await previous;
+        } catch (error) {
+            if (error instanceof MessageDeliveryError && error.retryable) {
+                // If the previous message failed to deliver, requeue all messages
+                // including the current one that was just enqueued
+                return this.requeue();
+            }
+
+            throw error;
+        }
+
+        if (this.closed) {
+            throw MessageDeliveryError.retryable('Connection deliberately closed.');
+        }
+
+        try {
+            const result = await this.channel.publish(message);
+
+            this.dequeue();
+
+            return result;
+        } catch (error) {
+            if (!(error instanceof MessageDeliveryError) || !error.retryable) {
+                // Discard the message if it's non-retryable
+                this.dequeue();
+
+                if (!enqueue) {
+                    // If the message was not enqueued, suppress the error
+                    // so that the next message in the queue can be immediately
+                    return;
+                }
+            }
+
+            throw error;
+        }
+    }
+
     public async close(): Promise<void> {
         this.closed = true;
 
diff --git a/src/channel/retryChannel.ts b/src/channel/retryChannel.ts
index daec4b0c..24687013 100644
--- a/src/channel/retryChannel.ts
+++ b/src/channel/retryChannel.ts
@@ -42,7 +42,7 @@ export class RetryChannel<T> implements OutputChannel<T> {
 
         while (this.retryPolicy.shouldRetry(attempt, message, error)) {
             if (this.closed) {
-                throw MessageDeliveryError.nonRetryable('Connection deliberately closed.');
+                throw MessageDeliveryError.retryable('Connection deliberately closed.');
             }
 
             const delay = this.retryPolicy.getDelay(attempt);
@@ -59,7 +59,7 @@ export class RetryChannel<T> implements OutputChannel<T> {
                                 // Cancel delay immediately when the channel is closed
                                 window.clearInterval(closeWatcher);
 
-                                reject(MessageDeliveryError.nonRetryable('Connection deliberately closed.'));
+                                reject(MessageDeliveryError.retryable('Connection deliberately closed.'));
                             }
                         },
                         0,
diff --git a/test/channel/guaranteedChannel.test.ts b/test/channel/guaranteedChannel.test.ts
index 59aaa3cc..ab2d858a 100644
--- a/test/channel/guaranteedChannel.test.ts
+++ b/test/channel/guaranteedChannel.test.ts
@@ -66,7 +66,7 @@ describe('A guaranteed channel', () => {
         await channel.close();
 
         await expect(promise).rejects.toThrowWithMessage(MessageDeliveryError, 'Connection deliberately closed.');
-        await expect(promise).rejects.toHaveProperty('retryable', false);
+        await expect(promise).rejects.toHaveProperty('retryable', true);
     });
 
     it('should close the output channel on close', async () => {
diff --git a/test/channel/queuedChannel.test.ts b/test/channel/queuedChannel.test.ts
index deae745a..4eb22239 100644
--- a/test/channel/queuedChannel.test.ts
+++ b/test/channel/queuedChannel.test.ts
@@ -1,12 +1,13 @@
 import {InMemoryQueue, CapacityRestrictedQueue} from '../../src/queue';
 import {QueuedChannel, OutputChannel, MessageDeliveryError} from '../../src/channel';
+import {Logger} from '../../src/logging';
 
 describe('A queued channel', () => {
     afterEach(() => {
         jest.restoreAllMocks();
     });
 
-    it('should resume flushing from the last failed message', async () => {
+    it('should resume flushing from the oldest message', async () => {
         const outputChannel: OutputChannel<string> = {
             close: jest.fn().mockResolvedValue(undefined),
             publish: jest.fn()
@@ -14,21 +15,29 @@ describe('A queued channel', () => {
                 .mockRejectedValueOnce(new MessageDeliveryError('Rejected', true))
                 .mockResolvedValue(undefined),
         };
-        const channel = new QueuedChannel(outputChannel, new InMemoryQueue('foo', 'bar'));
+        const queue = new InMemoryQueue('foo', 'bar');
+        const channel = new QueuedChannel(outputChannel, queue);
+
+        await expect(channel.flush()).rejects.toThrowWithMessage(MessageDeliveryError, 'Rejected');
 
-        await expect(channel.flush()).rejects.toEqual(expect.any(Error));
         expect(outputChannel.publish).toHaveBeenNthCalledWith(1, 'foo');
         expect(outputChannel.publish).toHaveBeenNthCalledWith(2, 'bar');
 
+        expect(outputChannel.publish).toHaveBeenCalledTimes(2);
+        expect(queue.isEmpty()).toBe(false);
+        expect(queue.peek()).toBe('bar');
+
         await channel.flush();
 
-        expect(outputChannel.publish).toHaveBeenNthCalledWith(3, 'bar');
+        expect(outputChannel.publish).toHaveBeenCalledTimes(3);
+        expect(queue.isEmpty()).toBe(true);
 
-        await channel.flush();
+        await expect(channel.publish('baz')).resolves.toBeUndefined();
 
-        expect(outputChannel.publish).toHaveBeenNthCalledWith(3, 'bar');
+        expect(outputChannel.publish).toHaveBeenNthCalledWith(4, 'baz');
 
-        expect(outputChannel.publish).toHaveBeenCalledTimes(3);
+        expect(outputChannel.publish).toHaveBeenCalledTimes(4);
+        expect(queue.isEmpty()).toBe(true);
     });
 
     it('should do nothing when flushing an empty queue', async () => {
@@ -123,30 +132,30 @@ describe('A queued channel', () => {
         await expect(promise).rejects.toHaveProperty('retryable', false);
     });
 
-    it('should fail to publish messages if queue has pending messages', async () => {
+    it('should automatically requeue messages on the first publish', async () => {
         const outputChannel: OutputChannel<string> = {
             close: jest.fn().mockResolvedValue(undefined),
             publish: jest.fn().mockResolvedValue(undefined),
         };
-        const channel = new QueuedChannel(outputChannel, new InMemoryQueue('foo'));
-
-        const promise = channel.publish('bar');
 
-        await expect(promise).rejects.toThrowWithMessage(MessageDeliveryError, 'The queue must be flushed.');
-        await expect(promise).rejects.toHaveProperty('retryable', true);
+        const queue = new InMemoryQueue('foo', 'bar');
+        const channel = new QueuedChannel(outputChannel, queue);
 
-        await channel.flush();
+        await expect(channel.publish('baz')).resolves.toBeUndefined();
 
         expect(outputChannel.publish).toHaveBeenNthCalledWith(1, 'foo');
         expect(outputChannel.publish).toHaveBeenNthCalledWith(2, 'bar');
+        expect(outputChannel.publish).toHaveBeenNthCalledWith(3, 'baz');
 
-        await channel.publish('baz');
+        expect(queue.isEmpty()).toBe(true);
 
-        expect(outputChannel.publish).toHaveBeenNthCalledWith(3, 'baz');
-        expect(outputChannel.publish).toHaveBeenCalledTimes(3);
+        await channel.publish('qux');
+
+        expect(outputChannel.publish).toHaveBeenNthCalledWith(4, 'qux');
+        expect(outputChannel.publish).toHaveBeenCalledTimes(4);
     });
 
-    it('should publish messages if queue has no pending messages', async () => {
+    it('should publish messages immediately if queue has no pending messages', async () => {
         const outputChannel: OutputChannel<string> = {
             close: jest.fn().mockResolvedValue(undefined),
             publish: jest.fn().mockResolvedValue(undefined),
@@ -166,16 +175,169 @@ describe('A queued channel', () => {
         expect(outputChannel.publish).toHaveBeenCalledTimes(2);
     });
 
-    it('should close the output channel and wait for pending messages', async () => {
+    it('should require a flush after a failed, non-retryable message', async () => {
+        const logger: Logger = {
+            debug: jest.fn(),
+            info: jest.fn(),
+            warn: jest.fn(),
+            error: jest.fn(),
+        };
+
         const outputChannel: OutputChannel<string> = {
             close: jest.fn().mockResolvedValue(undefined),
-            publish: jest.fn().mockResolvedValue(undefined),
+            publish: jest.fn()
+                .mockImplementationOnce(
+                    () => new Promise((_, reject) => {
+                        setTimeout(() => reject(new Error('Failed')), 1);
+                    }),
+                )
+                .mockResolvedValue(undefined),
         };
-        const channel = new QueuedChannel(outputChannel, new InMemoryQueue('foo'));
+
+        const channel = new QueuedChannel(outputChannel, new InMemoryQueue(), logger);
+
+        await expect(channel.publish('foo')).rejects.toEqual(expect.any(Error));
+        await expect(channel.publish('bar')).rejects.toEqual(expect.any(Error));
+
+        expect(outputChannel.publish).toHaveBeenCalledTimes(1);
+        expect(outputChannel.publish).toHaveBeenNthCalledWith(1, 'foo');
+
+        await channel.flush();
+
+        expect(outputChannel.publish).toHaveBeenCalledTimes(2);
+        expect(outputChannel.publish).toHaveBeenNthCalledWith(2, 'bar');
+    });
+
+    it('should resume processing on re-enqueued message errors', async () => {
+        const outputChannel: OutputChannel<string> = {
+            close: jest.fn().mockResolvedValue(undefined),
+            publish: jest.fn()
+                .mockRejectedValueOnce(new Error('Failed'))
+                .mockRejectedValueOnce(new Error('Failed'))
+                .mockResolvedValue(undefined),
+        };
+
+        const queue = new InMemoryQueue('foo', 'bar');
+        const channel = new QueuedChannel(outputChannel, queue);
+
+        await expect(channel.publish('baz')).resolves.toBeUndefined();
+
+        expect(outputChannel.publish).toHaveBeenCalledTimes(3);
+        expect(outputChannel.publish).toHaveBeenNthCalledWith(1, 'foo');
+        expect(outputChannel.publish).toHaveBeenNthCalledWith(2, 'bar');
+        expect(outputChannel.publish).toHaveBeenNthCalledWith(3, 'baz');
+
+        expect(queue.isEmpty()).toBe(true);
+    });
+
+    it('should flush all non-retryable messages even if an error occurs', async () => {
+        const outputChannel: OutputChannel<string> = {
+            close: jest.fn().mockResolvedValue(undefined),
+            publish: jest.fn()
+                .mockRejectedValueOnce(new Error('Failed'))
+                .mockRejectedValueOnce(new Error('Failed')),
+        };
+
+        const queue = new InMemoryQueue('foo', 'bar');
+        const channel = new QueuedChannel(outputChannel, queue);
 
         await expect(channel.flush()).resolves.toBeUndefined();
 
-        await channel.close();
+        expect(outputChannel.publish).toHaveBeenCalledTimes(2);
+        expect(outputChannel.publish).toHaveBeenNthCalledWith(1, 'foo');
+        expect(outputChannel.publish).toHaveBeenNthCalledWith(2, 'bar');
+
+        expect(queue.isEmpty()).toBe(true);
+    });
+
+    it('should not dequeue messages if an retryable error occurs', async () => {
+        const outputChannel: OutputChannel<string> = {
+            close: jest.fn().mockResolvedValue(undefined),
+            publish: jest.fn()
+                .mockResolvedValueOnce(undefined)
+                .mockRejectedValueOnce(new MessageDeliveryError('Rejected', true))
+                .mockResolvedValueOnce(undefined),
+        };
+
+        const queue = new InMemoryQueue('foo');
+        const channel = new QueuedChannel(outputChannel, queue);
+
+        const promise = channel.publish('bar');
+
+        await expect(promise).rejects.toEqual(expect.any(MessageDeliveryError));
+
+        expect(outputChannel.publish).toHaveBeenCalledTimes(2);
+        expect(outputChannel.publish).toHaveBeenNthCalledWith(1, 'foo');
+        expect(outputChannel.publish).toHaveBeenNthCalledWith(2, 'bar');
+
+        expect(queue.length()).toBe(1);
+        expect(queue.peek()).toBe('bar');
+
+        await expect(channel.flush()).resolves.toBeUndefined();
+
+        expect(outputChannel.publish).toHaveBeenCalledTimes(3);
+        expect(outputChannel.publish).toHaveBeenNthCalledWith(3, 'bar');
+
+        expect(queue.isEmpty()).toBe(true);
+    });
+
+    it('should requeue messages if a retryable error occurs', async () => {
+        const outputChannel: OutputChannel<string> = {
+            close: jest.fn().mockResolvedValue(undefined),
+            publish: jest.fn()
+                .mockResolvedValueOnce(undefined)
+                .mockRejectedValueOnce(new MessageDeliveryError('Rejected', true))
+                .mockResolvedValue(undefined),
+        };
+
+        const queue = new InMemoryQueue('foo');
+        const channel = new QueuedChannel(outputChannel, queue);
+
+        await expect(channel.publish('bar')).rejects.toEqual(expect.any(MessageDeliveryError));
+
+        expect(outputChannel.publish).toHaveBeenCalledTimes(2);
+        expect(outputChannel.publish).toHaveBeenNthCalledWith(1, 'foo');
+        expect(outputChannel.publish).toHaveBeenNthCalledWith(2, 'bar');
+
+        expect(queue.length()).toBe(1);
+        expect(queue.peek()).toBe('bar');
+
+        await expect(channel.publish('baz')).resolves.toBeUndefined();
+
+        expect(outputChannel.publish).toHaveBeenCalledTimes(4);
+        expect(outputChannel.publish).toHaveBeenNthCalledWith(3, 'bar');
+        expect(outputChannel.publish).toHaveBeenNthCalledWith(4, 'baz');
+
+        expect(queue.isEmpty()).toBe(true);
+    });
+
+    it('should close the output channel and wait for pending messages', async () => {
+        const outputChannel: OutputChannel<string> = {
+            close: jest.fn().mockResolvedValue(undefined),
+            publish: jest.fn()
+                .mockImplementationOnce(
+                    () => new Promise(resolve => {
+                        setTimeout(resolve, 2);
+                    }),
+                ),
+        };
+
+        const queue = new InMemoryQueue();
+        const channel = new QueuedChannel(outputChannel, queue);
+
+        const firstPromise = channel.publish('foo');
+        const secondPromise = channel.publish('bar');
+
+        const close = new Promise(resolve => { setTimeout(() => resolve(channel.close()), 1); });
+
+        await expect(firstPromise).resolves.toBeUndefined();
+        await expect(secondPromise).rejects.toThrowWithMessage(MessageDeliveryError, 'Connection deliberately closed.');
+        await expect(close).resolves.toBeUndefined();
+
+        expect(outputChannel.publish).toHaveBeenCalledTimes(1);
+
+        expect(queue.length()).toBe(1);
+        expect(queue.peek()).toBe('bar');
 
         expect(outputChannel.close).toHaveBeenCalled();
     });
diff --git a/test/channel/retryChannel.test.ts b/test/channel/retryChannel.test.ts
index 92b68dbd..fb9e918e 100644
--- a/test/channel/retryChannel.test.ts
+++ b/test/channel/retryChannel.test.ts
@@ -76,7 +76,7 @@ describe('A retry channel', () => {
         await channel.close();
 
         await expect(promise).rejects.toThrowWithMessage(MessageDeliveryError, 'Connection deliberately closed.');
-        await expect(promise).rejects.toHaveProperty('retryable', false);
+        await expect(promise).rejects.toHaveProperty('retryable', true);
     });
 
     it('should fail to publish a message if the channel is closed while retrying', async () => {
@@ -96,7 +96,7 @@ describe('A retry channel', () => {
         await channel.close();
 
         await expect(promise).rejects.toThrowWithMessage(MessageDeliveryError, 'Connection deliberately closed.');
-        await expect(promise).rejects.toHaveProperty('retryable', false);
+        await expect(promise).rejects.toHaveProperty('retryable', true);
     });
 
     it('should fail to publish a message if maximum retry attempts is reached', async () => {