diff --git a/internal/user/cooldown.go b/internal/user/cooldown.go
new file mode 100644
index 00000000..a0fd389a
--- /dev/null
+++ b/internal/user/cooldown.go
@@ -0,0 +1,62 @@
+// Copyright (c) 2023 Proton AG
+//
+// This file is part of Proton Mail Bridge.
+//
+// Proton Mail Bridge is free software: you can redistribute it and/or modify
+// it under the terms of the GNU General Public License as published by
+// the Free Software Foundation, either version 3 of the License, or
+// (at your option) any later version.
+//
+// Proton Mail Bridge is distributed in the hope that it will be useful,
+// but WITHOUT ANY WARRANTY; without even the implied warranty of
+// MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+// GNU General Public License for more details.
+//
+// You should have received a copy of the GNU General Public License
+// along with Proton Mail Bridge.  If not, see <https://www.gnu.org/licenses/>.
+
+package user
+
+import (
+	"math/rand"
+	"time"
+)
+
+const SyncRetryCooldown = 20 * time.Second
+
+type cooldownProvider interface {
+	GetNextWaitTime() time.Duration
+}
+
+func jitter(max int) time.Duration {
+	return time.Duration(rand.Intn(max)) * time.Second //nolint:gosec
+}
+
+type expCooldown struct {
+	count int
+}
+
+func (c *expCooldown) GetNextWaitTime() time.Duration {
+	waitTimes := []time.Duration{
+		20 * time.Second,
+		40 * time.Second,
+		80 * time.Second,
+		160 * time.Second,
+		300 * time.Second,
+		600 * time.Second,
+	}
+
+	last := len(waitTimes) - 1
+
+	if c.count >= last {
+		return waitTimes[last] + jitter(10)
+	}
+
+	c.count++
+
+	return waitTimes[c.count-1] + jitter(10)
+}
+
+type noCooldown struct{}
+
+func (c *noCooldown) GetNextWaitTime() time.Duration { return time.Millisecond }
diff --git a/internal/user/sync.go b/internal/user/sync.go
index 717a677a..f224f1d4 100644
--- a/internal/user/sync.go
+++ b/internal/user/sync.go
@@ -439,7 +439,18 @@ func (user *User) syncMessages(
 		metadataChunks := xslices.Chunk(messageIDs, MetadataDataPageSize)
 		for i, metadataChunk := range metadataChunks {
 			logrus.Debugf("Metadata Request (%v of %v), previous: %v", i, len(metadataChunks), len(downloadReq.ids))
+
+			cooldown := expCooldown{}
+
 			metadata, err := client.GetMessageMetadataPage(ctx, 0, len(metadataChunk), proton.MessageFilter{ID: metadataChunk})
+			for is429Error(err) {
+				wait := cooldown.GetNextWaitTime()
+				logrus.WithError(err).Warnf("Retrying in %v to download message metadata for chunk %v", wait, i)
+				sleepCtx(ctx, wait)
+
+				metadata, err = client.GetMessageMetadataPage(ctx, 0, len(metadataChunk), proton.MessageFilter{ID: metadataChunk})
+			}
+
 			if err != nil {
 				logrus.WithError(err).Errorf("Failed to download message metadata for chunk %v", i)
 				downloadReq.err = err
diff --git a/internal/user/sync_downloader.go b/internal/user/sync_downloader.go
index e84450bb..0084ab73 100644
--- a/internal/user/sync_downloader.go
+++ b/internal/user/sync_downloader.go
@@ -103,7 +103,7 @@ func startSyncDownloader(
 				return
 			}
 
-			batch, err := downloadMessagesStage2(ctx, result, downloader, cache, SyncRetryCooldown)
+			batch, err := downloadMessagesStage2(ctx, result, downloader, cache, &expCooldown{})
 			if err != nil {
 				errorCh <- err
 				return
@@ -281,7 +281,7 @@ func downloadMessagesStage2(
 	state []downloadResult,
 	downloader MessageDownloader,
 	cache *SyncDownloadCache,
-	coolDown time.Duration,
+	cooldown cooldownProvider,
 ) ([]proton.FullMessage, error) {
 	logrus.Debug("Entering download stage 2")
 	var retryList []int
@@ -289,7 +289,7 @@ func downloadMessagesStage2(
 
 	for {
 		if shouldWaitBeforeRetry {
-			time.Sleep(coolDown)
+			time.Sleep(cooldown.GetNextWaitTime())
 		}
 
 		retryList = nil
diff --git a/internal/user/sync_downloader_test.go b/internal/user/sync_downloader_test.go
index c03d6061..76a9b6a4 100644
--- a/internal/user/sync_downloader_test.go
+++ b/internal/user/sync_downloader_test.go
@@ -23,7 +23,6 @@ import (
 	"io"
 	"strings"
 	"testing"
-	"time"
 
 	"github.com/ProtonMail/gluon/async"
 	"github.com/ProtonMail/go-proton-api"
@@ -143,7 +142,7 @@ func TestSyncDownloader_Stage2_Everything200(t *testing.T) {
 		},
 	}
 
-	result, err := downloadMessagesStage2(ctx, downloadResult, messageDownloader, cache, time.Millisecond)
+	result, err := downloadMessagesStage2(ctx, downloadResult, messageDownloader, cache, &noCooldown{})
 	require.NoError(t, err)
 	require.Equal(t, 2, len(result))
 }
@@ -171,7 +170,7 @@ func TestSyncDownloader_Stage2_Not429(t *testing.T) {
 		},
 	}
 
-	_, err := downloadMessagesStage2(ctx, downloadResult, messageDownloader, cache, time.Millisecond)
+	_, err := downloadMessagesStage2(ctx, downloadResult, messageDownloader, cache, &noCooldown{})
 	require.Error(t, err)
 	require.Equal(t, msgErr, err)
 }
@@ -195,7 +194,7 @@ func TestSyncDownloader_Stage2_API500(t *testing.T) {
 		},
 	}
 
-	_, err := downloadMessagesStage2(ctx, downloadResult, messageDownloader, cache, time.Millisecond)
+	_, err := downloadMessagesStage2(ctx, downloadResult, messageDownloader, cache, &noCooldown{})
 	require.Error(t, err)
 	require.Equal(t, msgErr, err)
 }
@@ -303,7 +302,7 @@ func TestSyncDownloader_Stage2_Some429(t *testing.T) {
 		})
 	}
 
-	messages, err := downloadMessagesStage2(ctx, downloadResult, messageDownloader, cache, time.Millisecond)
+	messages, err := downloadMessagesStage2(ctx, downloadResult, messageDownloader, cache, &noCooldown{})
 	require.NoError(t, err)
 	require.Equal(t, 3, len(messages))
 
@@ -381,7 +380,7 @@ func TestSyncDownloader_Stage2_ErrorOnNon429MessageDownload(t *testing.T) {
 		messageDownloader.EXPECT().GetMessage(gomock.Any(), gomock.Eq("Msg3")).Times(1).Return(proton.Message{}, err500)
 	}
 
-	messages, err := downloadMessagesStage2(ctx, downloadResult, messageDownloader, cache, time.Millisecond)
+	messages, err := downloadMessagesStage2(ctx, downloadResult, messageDownloader, cache, &noCooldown{})
 	require.Error(t, err)
 	require.Empty(t, 0, messages)
 }
@@ -424,7 +423,7 @@ func TestSyncDownloader_Stage2_ErrorOnNon429AttachmentDownload(t *testing.T) {
 	// 500 for second attachment
 	messageDownloader.EXPECT().GetAttachmentInto(gomock.Any(), gomock.Eq("A4"), gomock.Any()).Times(1).Return(err500)
 
-	messages, err := downloadMessagesStage2(ctx, downloadResult, messageDownloader, cache, time.Millisecond)
+	messages, err := downloadMessagesStage2(ctx, downloadResult, messageDownloader, cache, &noCooldown{})
 	require.Error(t, err)
 	require.Empty(t, 0, messages)
 }
diff --git a/internal/user/user.go b/internal/user/user.go
index 0399fba1..6ae06287 100644
--- a/internal/user/user.go
+++ b/internal/user/user.go
@@ -55,10 +55,6 @@ var (
 	EventJitter = 20 * time.Second // nolint:gochecknoglobals,revive
 )
 
-const (
-	SyncRetryCooldown = 20 * time.Second
-)
-
 type User struct {
 	log *logrus.Entry
 
@@ -244,13 +240,16 @@ func New(
 				return
 			}
 
+			cooldown := expCooldown{}
+
 			for {
 				if err := ctx.Err(); err != nil {
 					user.log.WithError(err).Error("Sync aborted")
 					return
 				} else if err := user.doSync(ctx); err != nil {
-					user.log.WithError(err).Error("Failed to sync, will retry later")
-					sleepCtx(ctx, SyncRetryCooldown)
+					wait := cooldown.GetNextWaitTime()
+					user.log.WithField("retry-after", wait).WithError(err).Error("Failed to sync, will retry later")
+					sleepCtx(ctx, wait)
 				} else {
 					user.log.Info("Sync complete, starting API event stream")
 					return