diff --git a/apps/server/Services/AliasVault.SmtpService/Handlers/DatabaseMessageStore.cs b/apps/server/Services/AliasVault.SmtpService/Handlers/DatabaseMessageStore.cs
index 3a5a23b16..bfd696698 100644
--- a/apps/server/Services/AliasVault.SmtpService/Handlers/DatabaseMessageStore.cs
+++ b/apps/server/Services/AliasVault.SmtpService/Handlers/DatabaseMessageStore.cs
@@ -189,8 +189,11 @@ public class DatabaseMessageStore(ILogger<DatabaseMessageStore> logger, Config c
         {
             if (email.MessagePlain != null && !string.IsNullOrEmpty(email.MessagePlain) && email.MessagePlain.Length > 3)
             {
+                // Decode HTML entities (e.g., &#39; -> ', &amp; -> &)
+                string plainToPlainText = System.Net.WebUtility.HtmlDecode(email.MessagePlain);
+
                 // Replace any newline characters with a space
-                string plainToPlainText = Regex.Replace(email.MessagePlain, @"\t|\n|\r", " ", RegexOptions.NonBacktracking);
+                plainToPlainText = Regex.Replace(plainToPlainText, @"\t|\n|\r", " ", RegexOptions.NonBacktracking);
 
                 // Remove all "-" or "=" characters if there are 3 or more in a row
                 plainToPlainText = Regex.Replace(plainToPlainText, @"-{3,}|\={3,}", string.Empty, RegexOptions.NonBacktracking);
@@ -212,6 +215,9 @@ public class DatabaseMessageStore(ILogger<DatabaseMessageStore> logger, Config c
             {
                 string htmlToPlainText = Uglify.HtmlToText(email.MessageHtml).ToString();
 
+                // Decode HTML entities (e.g., &#39; -> ', &amp; -> &)
+                htmlToPlainText = System.Net.WebUtility.HtmlDecode(htmlToPlainText);
+
                 // Replace any newline characters with a space
                 htmlToPlainText = Regex.Replace(htmlToPlainText, @"\t|\n|\r", string.Empty, RegexOptions.NonBacktracking);