diff --git a/DiscordChatExporter.Core/Exporting/ChannelExporter.cs b/DiscordChatExporter.Core/Exporting/ChannelExporter.cs
index 4a434a97..9a8aa37c 100644
--- a/DiscordChatExporter.Core/Exporting/ChannelExporter.cs
+++ b/DiscordChatExporter.Core/Exporting/ChannelExporter.cs
@@ -55,24 +55,32 @@ public class ChannelExporter(DiscordClient discord)
                     );
                     if (lastMessageSnowflake != null)
                     {
-                        request.LastPriorMessage = lastMessageSnowflake.Value;
-
-                        if (!request.Channel.MayHaveMessagesAfter(request.LastPriorMessage.Value))
+                        if (!request.Channel.MayHaveMessagesAfter(lastMessageSnowflake.Value))
                         {
                             logger.IncrementCounter(ExportResult.UpdateExportSkip);
                             logger.LogInfo(request, "Existing export already up to date");
                             return;
                         }
-
+                        request.LastPriorMessage = lastMessageSnowflake.Value;
                         logger.LogInfo(
                             request,
                             "Appending existing export starting at "
                                 + lastMessageSnowflake.Value.ToDate()
                         );
-                        currentPartitionIndex = MessageExporter.GetPartitionCount(
-                            request.OutputFilePath
-                        );
                     }
+                    else
+                    {
+                        if (request.Channel.IsEmpty)
+                        {
+                            logger.IncrementCounter(ExportResult.UpdateExportSkip);
+                            logger.LogInfo(request, "Existing empty export already up to date");
+                            return;
+                        }
+                        logger.LogInfo(request, "Appending existing empty export.");
+                    }
+                    currentPartitionIndex = MessageExporter.GetPartitionCount(
+                        request.OutputFilePath
+                    );
                     break;
                 default:
                     throw new InvalidOperationException(
diff --git a/DiscordChatExporter.Core/Exporting/CsvMessageWriter.cs b/DiscordChatExporter.Core/Exporting/CsvMessageWriter.cs
index 9df2bba3..ede7052c 100644
--- a/DiscordChatExporter.Core/Exporting/CsvMessageWriter.cs
+++ b/DiscordChatExporter.Core/Exporting/CsvMessageWriter.cs
@@ -142,10 +142,12 @@ internal partial class CsvMessageWriter(Stream stream, ExportContext context)
     {
         try
         {
-            var fileLines = File.ReadAllLines(filePath)
-                .SkipWhile(string.IsNullOrWhiteSpace)
-                .ToArray();
-            if (fileLines.Length <= HeaderSize)
+            var fileLines = File.ReadAllLines(filePath);
+            var fileContainsMessages = fileLines
+                .Where(line => !string.IsNullOrWhiteSpace(line))
+                .Skip(HeaderSize)
+                .Any();
+            if (!fileContainsMessages)
                 return null;
 
             const string columnPattern = "(?:[^\"]?(?:\"\")?)*";
@@ -155,7 +157,9 @@ internal partial class CsvMessageWriter(Stream stream, ExportContext context)
             );
             var messageDateRegex = new Regex(messageDatePattern);
 
-            var timestampMatch = messageDateRegex.Match(fileLines[^1]);
+            var timestampMatch = messageDateRegex.Match(
+                fileLines.Last(line => !string.IsNullOrWhiteSpace(line))
+            );
             var timestampString = timestampMatch.Groups[1].Value;
             var timestamp = DateTimeOffset.Parse(timestampString);
             return Snowflake.FromDate(timestamp, true);
diff --git a/DiscordChatExporter.Core/Exporting/HtmlMessageWriter.cs b/DiscordChatExporter.Core/Exporting/HtmlMessageWriter.cs
index e6916fd2..f8357a99 100644
--- a/DiscordChatExporter.Core/Exporting/HtmlMessageWriter.cs
+++ b/DiscordChatExporter.Core/Exporting/HtmlMessageWriter.cs
@@ -179,6 +179,8 @@ internal partial class HtmlMessageWriter(Stream stream, ExportContext context, s
             var messageDateRegex = MessageDateRegex();
 
             var timestampMatches = messageDateRegex.Matches(fileContent);
+            if (timestampMatches.Count == 0)
+                return null;
             var timestampString = timestampMatches[^1].Groups[1].Value;
             var timestamp = DateTimeOffset.Parse(timestampString);
             return Snowflake.FromDate(timestamp, true);
diff --git a/DiscordChatExporter.Core/Exporting/MessageGroupTemplate.cshtml b/DiscordChatExporter.Core/Exporting/MessageGroupTemplate.cshtml
index e0730553..4a7d2558 100644
--- a/DiscordChatExporter.Core/Exporting/MessageGroupTemplate.cshtml
+++ b/DiscordChatExporter.Core/Exporting/MessageGroupTemplate.cshtml
@@ -240,6 +240,7 @@
                             }
 
                             @* Timestamp *@
+                            @* Don't change this without changing the corresponding detection in the HtmlMessageWriter *@
                             <span class="chatlog__timestamp" title="@FormatDate(message.Timestamp, "f")"><a href="#chatlog__message-container-@message.Id">@FormatDate(message.Timestamp)</a></span>
                         </div>
                     }
diff --git a/DiscordChatExporter.Core/Exporting/PlainTextMessageWriter.cs b/DiscordChatExporter.Core/Exporting/PlainTextMessageWriter.cs
index f96248ad..a2dc5976 100644
--- a/DiscordChatExporter.Core/Exporting/PlainTextMessageWriter.cs
+++ b/DiscordChatExporter.Core/Exporting/PlainTextMessageWriter.cs
@@ -16,6 +16,7 @@ internal partial class PlainTextMessageWriter(Stream stream, ExportContext conte
     : MessageWriter(stream, context)
 {
     private const int HeaderSize = 4;
+    private const int FooterSize = 3;
 
     private readonly TextWriter _writer = new StreamWriter(stream);
 
@@ -306,13 +307,17 @@ internal partial class PlainTextMessageWriter(Stream stream, ExportContext conte
     public static Snowflake? GetLastMessageDate(string filePath)
     {
         var fileLines = File.ReadAllLines(filePath);
-        if (fileLines.SkipWhile(string.IsNullOrWhiteSpace).ToArray().Length <= HeaderSize)
+        var fileContainsMessages = fileLines
+            .Where(line => !string.IsNullOrWhiteSpace(line))
+            .Skip(HeaderSize + FooterSize)
+            .Any();
+        if (!fileContainsMessages)
             return null;
 
         var messageDateRegex = MessageDateRegex();
 
         // Find the last line with a message timestamp
-        for (var i = fileLines.Length - 1; i >= HeaderSize; i--)
+        for (var i = fileLines.Length - 1 - FooterSize; i >= HeaderSize; i--)
         {
             var timestampMatch = messageDateRegex.Match(fileLines[i]);
             if (!timestampMatch.Success)