diff --git a/src/DiscordArchiveManager/Services/JsonImportService.cs b/src/DiscordArchiveManager/Services/JsonImportService.cs
index 23bc6f5..fcc6729 100644
--- a/src/DiscordArchiveManager/Services/JsonImportService.cs
+++ b/src/DiscordArchiveManager/Services/JsonImportService.cs
@@ -72,20 +72,32 @@ public class JsonImportService
                 // Upsert Channel
                 await UpsertChannelAsync(export.Channel, export.Guild.Id);
 
-                // Process messages
+                // Process messages - save after each to isolate any issues
                 var processedCount = 0;
                 foreach (var message in export.Messages)
                 {
-                    if (await ProcessMessageAsync(message, export.Channel.Id, jsonFilePath, imageRoot))
+                    try
                     {
-                        processedCount++;
+                        if (await ProcessMessageAsync(message, export.Channel.Id, jsonFilePath, imageRoot))
+                        {
+                            await _context.SaveChangesAsync();
+                            processedCount++;
+                        }
+                    }
+                    catch (DbUpdateException ex) when (ex.InnerException is Microsoft.Data.SqlClient.SqlException sqlEx && sqlEx.Number == 2601)
+                    {
+                        // Duplicate key - log and continue
+                        _logger.LogWarning("Duplicate key error for message {MessageId}, skipping: {Error}",
+                            message.Id, sqlEx.Message);
+                        _context.ChangeTracker.Clear();
+                        // Re-upsert guild and channel as they were cleared
+                        await UpsertGuildAsync(export.Guild);
+                        await UpsertChannelAsync(export.Channel, export.Guild.Id);
                     }
                 }
 
                 _logger.LogInformation("Processed {Count} new messages", processedCount);
 
-                await _context.SaveChangesAsync();
-
                 // Archive the file
                 var archivePath = _archiveService.ArchiveExport(jsonFilePath, archiveRoot);
 
@@ -106,6 +118,9 @@ public class JsonImportService
             catch (Exception ex)
             {
                 await transaction.RollbackAsync();
+                _context.ChangeTracker.Clear(); // Clear tracked entities to prevent cascading failures
+                _processedMessages.Clear(); // Clear the session tracking
+                _addedReactions.Clear();
                 _logger.LogError(ex, "Error processing file, rolled back transaction: {Path}", jsonFilePath);
                 throw;
             }