diff --git a/app/src/main/java/org/thoughtcrime/securesms/linkdevice/LinkDeviceFragment.kt b/app/src/main/java/org/thoughtcrime/securesms/linkdevice/LinkDeviceFragment.kt
index 69134de483..4657a2f673 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/linkdevice/LinkDeviceFragment.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/linkdevice/LinkDeviceFragment.kt
@@ -71,6 +71,7 @@ import org.thoughtcrime.securesms.BiometricDeviceLockContract
 import org.thoughtcrime.securesms.R
 import org.thoughtcrime.securesms.compose.ComposeFragment
 import org.thoughtcrime.securesms.linkdevice.LinkDeviceSettingsState.DialogState
+import org.thoughtcrime.securesms.util.CommunicationActions
 import org.thoughtcrime.securesms.util.DateUtils
 import org.thoughtcrime.securesms.util.navigation.safeNavigate
 import java.util.Locale
@@ -202,6 +203,10 @@ class LinkDeviceFragment : ComposeFragment() {
         onDeviceRemovalConfirmed = { device -> viewModel.removeDevice(device) },
         onSyncFailureRetryRequested = { viewModel.onSyncErrorRetryRequested() },
         onSyncFailureIgnored = { viewModel.onSyncErrorIgnored() },
+        onSyncFailureLearnMore = {
+          viewModel.onSyncErrorIgnored()
+          CommunicationActions.openBrowserLink(requireContext(), requireContext().getString(R.string.LinkDeviceFragment__learn_more_url))
+        },
         onSyncCancelled = { viewModel.onSyncCancelled() },
         onEditDevice = { device ->
           viewModel.setDeviceToEdit(device)
@@ -257,6 +262,7 @@ fun DeviceListScreen(
   onDeviceRemovalConfirmed: (Device) -> Unit = {},
   onSyncFailureRetryRequested: () -> Unit = {},
   onSyncFailureIgnored: () -> Unit = {},
+  onSyncFailureLearnMore: () -> Unit = {},
   onSyncCancelled: () -> Unit = {},
   onEditDevice: (Device) -> Unit = {},
   onDialogDismissed: () -> Unit = {}
@@ -281,7 +287,29 @@ fun DeviceListScreen(
           onDismiss = onSyncCancelled
         )
       }
-      is DialogState.SyncingFailed,
+      is DialogState.SyncingFailed -> {
+        if (state.dialogState.canRetry) {
+          Dialogs.SimpleAlertDialog(
+            title = stringResource(R.string.LinkDeviceFragment__sync_failure_title),
+            body = stringResource(R.string.LinkDeviceFragment__sync_failure_body),
+            confirm = stringResource(R.string.LinkDeviceFragment__sync_failure_retry_button),
+            onConfirm = onSyncFailureRetryRequested,
+            dismiss = stringResource(R.string.LinkDeviceFragment__sync_failure_dismiss_button),
+            onDismissRequest = onSyncFailureIgnored,
+            onDeny = onSyncFailureIgnored
+          )
+        } else {
+          Dialogs.SimpleAlertDialog(
+            title = stringResource(R.string.LinkDeviceFragment__sync_failure_title),
+            body = stringResource(R.string.LinkDeviceFragment__sync_failure_body_unretryable),
+            confirm = stringResource(R.string.LinkDeviceFragment__continue),
+            onConfirm = onSyncFailureIgnored,
+            dismiss = stringResource(R.string.LinkDeviceFragment__learn_more),
+            onDismissRequest = onSyncFailureIgnored,
+            onDeny = onSyncFailureLearnMore
+          )
+        }
+      }
       DialogState.SyncingTimedOut -> {
         Dialogs.SimpleAlertDialog(
           title = stringResource(R.string.LinkDeviceFragment__sync_failure_title),
diff --git a/app/src/main/java/org/thoughtcrime/securesms/linkdevice/LinkDeviceSettingsState.kt b/app/src/main/java/org/thoughtcrime/securesms/linkdevice/LinkDeviceSettingsState.kt
index ec077ff400..bf34cda402 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/linkdevice/LinkDeviceSettingsState.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/linkdevice/LinkDeviceSettingsState.kt
@@ -30,7 +30,7 @@ data class LinkDeviceSettingsState(
     data object Unlinking : DialogState
     data class SyncingMessages(val deviceId: Int, val deviceCreatedAt: Long) : DialogState
     data object SyncingTimedOut : DialogState
-    data class SyncingFailed(val deviceId: Int, val deviceCreatedAt: Long) : DialogState
+    data class SyncingFailed(val deviceId: Int, val deviceCreatedAt: Long, val canRetry: Boolean) : DialogState
     data class DeviceUnlinked(val deviceCreatedAt: Long) : DialogState
   }
 
diff --git a/app/src/main/java/org/thoughtcrime/securesms/linkdevice/LinkDeviceViewModel.kt b/app/src/main/java/org/thoughtcrime/securesms/linkdevice/LinkDeviceViewModel.kt
index dd0c7cc38d..4a4b2bfcad 100644
--- a/app/src/main/java/org/thoughtcrime/securesms/linkdevice/LinkDeviceViewModel.kt
+++ b/app/src/main/java/org/thoughtcrime/securesms/linkdevice/LinkDeviceViewModel.kt
@@ -313,9 +313,14 @@ class LinkDeviceViewModel : ViewModel() {
       is LinkDeviceRepository.LinkUploadArchiveResult.BadRequest,
       is LinkDeviceRepository.LinkUploadArchiveResult.NetworkError -> {
         Log.w(TAG, "[addDeviceWithSync] Failed to upload the archive! Result: $uploadResult")
+        val canRetry = uploadResult !is LinkDeviceRepository.LinkUploadArchiveResult.BackupCreationFailure
         _state.update {
           it.copy(
-            dialogState = DialogState.SyncingFailed(waitResult.id, waitResult.created)
+            dialogState = DialogState.SyncingFailed(
+              deviceId = waitResult.id,
+              deviceCreatedAt = waitResult.created,
+              canRetry = canRetry
+            )
           )
         }
       }
@@ -385,6 +390,7 @@ class LinkDeviceViewModel : ViewModel() {
       Log.i(TAG, "Alerting linked device of sync failure - will not retry")
       LinkDeviceRepository.sendTransferArchiveError(dialogState.deviceId, dialogState.deviceCreatedAt, TransferArchiveError.CONTINUE_WITHOUT_UPLOAD)
     }
+    loadDevices()
 
     _state.update {
       it.copy(
diff --git a/app/src/main/res/values/strings.xml b/app/src/main/res/values/strings.xml
index f48671a03a..f07641fa49 100644
--- a/app/src/main/res/values/strings.xml
+++ b/app/src/main/res/values/strings.xml
@@ -1010,8 +1010,13 @@
     <string name="LinkDeviceFragment__sync_failure_title">Message sync failed</string>
     <!-- Body of a dialog letting the user know that syncing messages to their linked device failed -->
     <string name="LinkDeviceFragment__sync_failure_body">Your messages couldn\'t be transferred to your linked device. You can try re-linking and transferring again, or continue without transferring your message history.</string>
+    <!-- Body of a dialog letting the user know that syncing messages to their linked device failed but the device was still able to be linked -->
+    <string name="LinkDeviceFragment__sync_failure_body_unretryable">Your device was successfully linked, but your messages could not be transferred.</string>
+    <!-- Text button in a dialog that, when pressed, will redirect to the Signal support page -->
+    <string name="LinkDeviceFragment__learn_more">Learn more</string>
+    <string name="LinkDeviceFragment__learn_more_url" translatable="false">https://support.signal.org/hc/articles/360007320551</string>
     <!-- Text button of a button in a dialog that, when pressed, will restart the process of linking a device -->
-    <string name="LinkDeviceFragment__sync_failure_retry_button">Try linking again</string>
+    <string name="LinkDeviceFragment__sync_failure_retry_button">Retry</string>
     <!-- Text button of a button in a dialog that, when pressed, will ignore syncing errors and link a new device without syncing message content -->
     <string name="LinkDeviceFragment__sync_failure_dismiss_button">Continue without transferring</string>
     <!-- Option in context menu to edit the name of a linked device -->