diff --git a/daemon/logger/ring.go b/daemon/logger/ring.go
index 8c19b543d6..7d7f839f36 100644
--- a/daemon/logger/ring.go
+++ b/daemon/logger/ring.go
@@ -8,6 +8,7 @@ import (
 
 const (
 	defaultRingMaxSize = 1e6 // 1MB
+	defaultQueueSize   = 1000
 )
 
 // RingLogger is a ring buffer that implements the Logger interface.
@@ -36,8 +37,11 @@ func (r *ringWithReader) ReadLogs(cfg ReadConfig) *LogWatcher {
 }
 
 func newRingLogger(driver Logger, logInfo Info, maxSize int64) *RingLogger {
+	if maxSize < 0 {
+		maxSize = defaultRingMaxSize
+	}
 	l := &RingLogger{
-		buffer:  newRing(maxSize),
+		buffer:  newRing(maxSize, defaultQueueSize),
 		l:       driver,
 		logInfo: logInfo,
 	}
@@ -49,9 +53,6 @@ func newRingLogger(driver Logger, logInfo Info, maxSize int64) *RingLogger {
 // NewRingLogger creates a new Logger that is implemented as a RingBuffer wrapping
 // the passed in logger.
 func NewRingLogger(driver Logger, logInfo Info, maxSize int64) Logger {
-	if maxSize < 0 {
-		maxSize = defaultRingMaxSize
-	}
 	l := newRingLogger(driver, logInfo, maxSize)
 	if _, ok := driver.(LogReader); ok {
 		return &ringWithReader{l}
@@ -141,21 +142,41 @@ type messageRing struct {
 	maxBytes  int64 // max buffer size
 	queue     []*Message
 	closed    bool
+
+	// head: index of the next message to dequeue from
+	// tail: index of the next message to enqueue to
+	// count: number of messages in the queue
+	head, tail, count int
+
+	// tracks the number of times the queue has been grown
+	// Used to determine if we can shrink the queue back down on dequeue
+	growCount int
+
+	dropped int64
 }
 
-func newRing(maxBytes int64) *messageRing {
-	queueSize := 1000
-	if maxBytes == 0 || maxBytes == 1 {
-		// With 0 or 1 max byte size, the maximum size of the queue would only ever be 1
-		// message long.
-		queueSize = 1
+func newRing(maxBytes int64, queueSize int) *messageRing {
+	if queueSize == 0 {
+		queueSize = defaultQueueSize
 	}
 
-	r := &messageRing{queue: make([]*Message, 0, queueSize), maxBytes: maxBytes}
+	r := &messageRing{queue: make([]*Message, queueSize), maxBytes: maxBytes}
 	r.wait = sync.NewCond(&r.mu)
 	return r
 }
 
+func (r *messageRing) isEmpty() bool {
+	return r.head == r.tail && !r.isFull()
+}
+
+func (r *messageRing) isFull() bool {
+	return r.count == cap(r.queue)
+}
+
+func (r *messageRing) next(i int) int {
+	return (i + 1) % cap(r.queue)
+}
+
 // Enqueue adds a message to the buffer queue
 // If the message is too big for the buffer it drops the new message.
 // If there are no messages in the queue and the message is still too big, it adds the message anyway.
@@ -167,14 +188,31 @@ func (r *messageRing) Enqueue(m *Message) error {
 		r.mu.Unlock()
 		return errClosed
 	}
-	if mSize+r.sizeBytes > r.maxBytes && len(r.queue) > 0 {
-		r.wait.Signal()
-		r.mu.Unlock()
-		return nil
+
+	// drop old messages until there is enough space for the new message
+	// This is not accounting for slots in the queue, just the size of the messages
+	for mSize+r.sizeBytes > r.maxBytes && !r.isEmpty() {
+		r.dequeue()
+		r.dropped++
 	}
 
-	r.queue = append(r.queue, m)
+	if r.isFull() {
+		// We've run out of space to store messages in the circular buffer even though we have not reached our byte limit.
+		// This means we need to resize the queue to make room for more messages.
+		//
+		r.growCount++
+		buf := make([]*Message, len(r.queue)*2)
+		r.copyTo(buf)
+		r.queue = buf
+		r.head = 0
+		r.tail = r.count
+	}
+
+	r.queue[r.tail] = m
+	r.tail = r.next(r.tail)
 	r.sizeBytes += mSize
+	r.count++
+
 	r.wait.Signal()
 	r.mu.Unlock()
 	return nil
@@ -185,7 +223,7 @@ func (r *messageRing) Enqueue(m *Message) error {
 // If the buffer is closed, it will return immediately.
 func (r *messageRing) Dequeue() (*Message, error) {
 	r.mu.Lock()
-	for len(r.queue) == 0 && !r.closed {
+	for r.isEmpty() && !r.closed {
 		r.wait.Wait()
 	}
 
@@ -194,13 +232,33 @@ func (r *messageRing) Dequeue() (*Message, error) {
 		return nil, errClosed
 	}
 
-	msg := r.queue[0]
-	r.queue = r.queue[1:]
-	r.sizeBytes -= int64(len(msg.Line))
+	msg := r.dequeue()
 	r.mu.Unlock()
 	return msg, nil
 }
 
+// callers must validate that there is at least one message in the queue
+// callers must hold the lock
+func (r *messageRing) dequeue() *Message {
+	msg := r.queue[r.head]
+	r.queue[r.head] = nil
+	r.head = r.next(r.head)
+	r.sizeBytes -= int64(len(msg.Line))
+	r.count--
+
+	if r.growCount > 0 && r.count <= cap(r.queue)/4 {
+		// We've shrunk the queue enough that we can resize it back down.
+		// This is to prevent the queue from growing too large and never shrinking back down.
+		buf := make([]*Message, cap(r.queue)/2)
+		r.copyTo(buf)
+		r.queue = buf
+		r.head = 0
+		r.tail = r.count
+		r.growCount--
+	}
+	return msg
+}
+
 var errClosed = errors.New("closed")
 
 // Close closes the buffer ensuring no new messages can be added.
@@ -217,14 +275,55 @@ func (r *messageRing) Close() {
 	r.mu.Unlock()
 }
 
+func (r *messageRing) Len() int {
+	r.mu.Lock()
+	defer r.mu.Unlock()
+	return r.count
+}
+
+func (r *messageRing) copyTo(buf []*Message) {
+	if r.isEmpty() {
+		return
+	}
+
+	// Here we have a circular buffer that we need to copy to the passed in slice.
+	// The assumption here is that `ls` is at least as large enough to hold all the messages in the queue.
+	// It maybe larger than the queue, but it must not be smaller.
+
+	// +---+---+---+---+---+---+---+---+---+---+
+	// | 0 | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 |
+	// +---+---+---+---+---+---+---+---+---+---+
+	//   ^                                   ^
+	//   |                                   |
+	// head                                tail
+
+	// The above example is a simplified view of the queue. The head is at index 0 (beginning) and the tail is at index 9 (end).
+	// In reality this could happen at any point in the queue. The head could be at index 5 and the tail at index 4.
+
+	// Copy from head marker of the slice
+	// Since this is a circular buffer we need to account for the wrap around.
+	if r.head < r.tail {
+		copy(buf, r.queue[r.head:r.tail])
+	} else {
+		n := copy(buf, r.queue[r.head:])
+		copy(buf[n:], r.queue[:r.tail])
+	}
+
+}
+
 // Drain drains all messages from the queue.
 // This can be used after `Close()` to get any remaining messages that were in queue.
 func (r *messageRing) Drain() []*Message {
 	r.mu.Lock()
-	ls := make([]*Message, 0, len(r.queue))
-	ls = append(ls, r.queue...)
+	ls := make([]*Message, r.count)
+
+	r.copyTo(ls)
+
 	r.sizeBytes = 0
-	r.queue = r.queue[:0]
+	r.head = 0
+	r.tail = 0
+	r.count = 0
+
 	r.mu.Unlock()
 	return ls
 }
diff --git a/daemon/logger/ring_test.go b/daemon/logger/ring_test.go
index eab2446234..84ec09399f 100644
--- a/daemon/logger/ring_test.go
+++ b/daemon/logger/ring_test.go
@@ -5,6 +5,9 @@ import (
 	"strconv"
 	"testing"
 	"time"
+
+	"gotest.tools/v3/assert"
+	is "gotest.tools/v3/assert/cmp"
 )
 
 type mockLogger struct{ c chan *Message }
@@ -34,9 +37,7 @@ func TestRingLogger(t *testing.T) {
 
 	select {
 	case msg := <-mockLog.c:
-		if string(msg.Line) != "1" {
-			t.Fatalf("got unexpected msg: %q", string(msg.Line))
-		}
+		assert.Equal(t, string(msg.Line), "3")
 	case <-time.After(100 * time.Millisecond):
 		t.Fatal("timeout reading log message")
 	}
@@ -46,102 +47,77 @@ func TestRingLogger(t *testing.T) {
 		t.Fatalf("expected no more messages in the queue, got: %q", string(msg.Line))
 	default:
 	}
+
+	assert.Equal(t, ring.buffer.dropped, int64(2))
 }
 
 func TestRingCap(t *testing.T) {
-	r := newRing(5)
+	r := newRing(5, 0)
 	for i := 0; i < 10; i++ {
 		// queue messages with "0" to "10"
-		// the "5" to "10" messages should be dropped since we only allow 5 bytes in the buffer
-		if err := r.Enqueue(&Message{Line: []byte(strconv.Itoa(i))}); err != nil {
-			t.Fatal(err)
-		}
+		// the "0" to "4" messages should be dropped since we only allow 5 bytes in the buffer
+		err := r.Enqueue(&Message{Line: []byte(strconv.Itoa(i))})
+		assert.NilError(t, err)
 	}
 
 	// should have messages in the queue for "0" to "4"
-	for i := 0; i < 5; i++ {
+	for i := 5; i < 10; i++ {
 		m, err := r.Dequeue()
-		if err != nil {
-			t.Fatal(err)
-		}
-		if string(m.Line) != strconv.Itoa(i) {
-			t.Fatalf("got unexpected message for iter %d: %s", i, string(m.Line))
-		}
+		assert.NilError(t, err)
+		assert.Equal(t, string(m.Line), strconv.Itoa(i))
 	}
 
 	// queue a message that's bigger than the buffer cap
-	if err := r.Enqueue(&Message{Line: []byte("hello world")}); err != nil {
-		t.Fatal(err)
-	}
+
+	err := r.Enqueue(&Message{Line: []byte("hello world")})
+	assert.NilError(t, err)
 
 	// queue another message that's bigger than the buffer cap
-	if err := r.Enqueue(&Message{Line: []byte("eat a banana")}); err != nil {
-		t.Fatal(err)
-	}
+	err = r.Enqueue(&Message{Line: []byte("eat a banana")})
+	assert.NilError(t, err)
 
 	m, err := r.Dequeue()
-	if err != nil {
-		t.Fatal(err)
-	}
-	if string(m.Line) != "hello world" {
-		t.Fatalf("got unexpected message: %s", string(m.Line))
-	}
-	if len(r.queue) != 0 {
-		t.Fatalf("expected queue to be empty, got: %d", len(r.queue))
-	}
+	assert.NilError(t, err)
+	assert.Equal(t, string(m.Line), "eat a banana")
+	assert.Equal(t, r.count, 0)
 }
 
 func TestRingClose(t *testing.T) {
-	r := newRing(1)
-	if err := r.Enqueue(&Message{Line: []byte("hello")}); err != nil {
-		t.Fatal(err)
-	}
+	r := newRing(1, 0)
+	err := r.Enqueue(&Message{Line: []byte("hello")})
+	assert.NilError(t, err)
+
 	r.Close()
-	if err := r.Enqueue(&Message{}); err != errClosed {
-		t.Fatalf("expected errClosed, got: %v", err)
-	}
-	if len(r.queue) != 1 {
-		t.Fatal("expected empty queue")
-	}
-	if m, err := r.Dequeue(); err == nil || m != nil {
-		t.Fatal("expected err on Dequeue after close")
-	}
+
+	assert.ErrorIs(t, r.Enqueue(&Message{}), errClosed)
+	assert.Equal(t, r.count, 1)
+
+	m, err := r.Dequeue()
+	assert.ErrorIs(t, err, errClosed)
+	assert.Assert(t, is.Nil(m))
 
 	ls := r.Drain()
-	if len(ls) != 1 {
-		t.Fatalf("expected one message: %v", ls)
-	}
-	if string(ls[0].Line) != "hello" {
-		t.Fatalf("got unexpected message: %s", string(ls[0].Line))
-	}
+	assert.Assert(t, is.Len(ls, 1))
+	assert.Equal(t, string(ls[0].Line), "hello")
 }
 
 func TestRingDrain(t *testing.T) {
-	r := newRing(5)
+	r := newRing(5, 0)
 	for i := 0; i < 5; i++ {
-		if err := r.Enqueue(&Message{Line: []byte(strconv.Itoa(i))}); err != nil {
-			t.Fatal(err)
-		}
+		err := r.Enqueue(&Message{Line: []byte(strconv.Itoa(i))})
+		assert.NilError(t, err)
 	}
 
 	ls := r.Drain()
-	if len(ls) != 5 {
-		t.Fatal("got unexpected length after drain")
-	}
+	assert.Assert(t, is.Len(ls, 5))
 
 	for i := 0; i < 5; i++ {
-		if string(ls[i].Line) != strconv.Itoa(i) {
-			t.Fatalf("got unexpected message at position %d: %s", i, string(ls[i].Line))
-		}
-	}
-	if r.sizeBytes != 0 {
-		t.Fatalf("expected buffer size to be 0 after drain, got: %d", r.sizeBytes)
+		assert.Check(t, is.Equal(string(ls[i].Line), strconv.Itoa(i)))
 	}
+	assert.Check(t, is.Equal(r.count, 0))
 
 	ls = r.Drain()
-	if len(ls) != 0 {
-		t.Fatalf("expected 0 messages on 2nd drain: %v", ls)
-	}
+	assert.Assert(t, is.Len(ls, 0))
 }
 
 type nopLogger struct{}