Save a copy of live-sent mail to the IMAP Sent folder

Co-Authored-By: Claude Sonnet 5.5 <noreply@anthropic.com>

config.example.ini

@@ -10,6 +10,9 @@ SMTP_FROM=danielcovington@postcardmojo.com
 SMTP_REPLY_TO=danielcovington@postcardmojo.com
 SMTP_TEST_TO=
 SMTP_SECRET_ID=primary_smtp
+IMAP_HOST=
+IMAP_PORT=993
+IMAP_SENT_FOLDER=Sent
 DB_PATH=data/MassMailer.mdb
 DB_PROVIDER=Microsoft.ACE.OLEDB.12.0
 DB_BITNESS=x86
@@ -29,6 +32,9 @@ BACKUP_DIR=backups
 # QUEUE_INTERVAL is the minimum number of seconds between attempts across
 # all campaigns using this SMTP account. TLS=on plus STARTTLS=on means the
 # sender must upgrade to TLS and fail closed if the server cannot do so.
+# IMAP_HOST enables saving a copy of each live-sent message to the Sent folder
+# over implicit-TLS IMAP, using SMTP_USER and the stored SMTP password. Leave it
+# empty to disable. A failed save is reported but never affects delivery status.
 # SMTP_REPLY_TO is the monitored mailbox confirmed by the owner.
 # Set SMTP_TEST_TO to an owner-controlled address before the internal transport test.
 # DB_PROVIDER and DB_BITNESS are checked before the HTA opens. On this PC,

tools/common.vbs

@@ -63,6 +63,7 @@ Function IsAllowedKey(key)
     IsAllowedKey = False
     For Each name In Array("SMTP_HOST", "SMTP_PORT", "SMTP_USER", "SMTP_TLS", _
         "SMTP_STARTTLS", "SMTP_FROM", "SMTP_REPLY_TO", "SMTP_TEST_TO", "SMTP_SECRET_ID", _
+        "IMAP_HOST", "IMAP_PORT", "IMAP_SENT_FOLDER", _
         "DB_PATH", "DB_PROVIDER", "DB_BITNESS", "QUEUE_INTERVAL", _
         "SEND_MODE", "DISPLAY_TIME_ZONE", "TEMPLATE_ROOT", _
         "TEMPLATE_IMAGE_MODE", "TEMPLATE_IMAGE_TYPES", _

tools/dispatch-once.ps1

@@ -163,6 +163,7 @@ try {
         Complete-DeliveryAttempt $db $reservedDelivery $reservedAttempt 'accepted' 'accepted'
         Complete-FinishedCampaigns $db
         Write-Output "SMTP accepted delivery $reservedDelivery. Next slot at $($next.ToString('o'))."
+        if ($Send) { $sentNote = Save-SentCopySafely $settings $password $message; if ($sentNote) { Write-Output $sentNote } }
     }
     catch {
         $code = if ($_.Exception -is [System.Net.Mail.SmtpException]) {

tools/mail-common.ps1

@@ -109,3 +109,113 @@ function Load-SmtpPassword {
         $connection.Dispose()
     }
 }
+
+function Get-MessageMimeBytes {
+    param([System.Net.Mail.MailMessage]$Message)
+    # Rewind inline image streams that the SMTP send already consumed.
+    foreach ($view in $Message.AlternateViews) {
+        $view.ContentStream.Position = 0
+        foreach ($resource in $view.LinkedResources) { $resource.ContentStream.Position = 0 }
+    }
+    $directory = Join-Path ([System.IO.Path]::GetTempPath()) ([guid]::NewGuid().ToString('N'))
+    $null = New-Item -ItemType Directory -Path $directory
+    $client = New-Object System.Net.Mail.SmtpClient
+    try {
+        $client.DeliveryMethod = [System.Net.Mail.SmtpDeliveryMethod]::SpecifiedPickupDirectory
+        $client.PickupDirectoryLocation = $directory
+        $client.Send($Message)
+        $file = Get-ChildItem -LiteralPath $directory -Filter '*.eml' | Select-Object -First 1
+        return [System.IO.File]::ReadAllBytes($file.FullName)
+    }
+    finally {
+        $client.Dispose()
+        Remove-Item -LiteralPath $directory -Recurse -Force -ErrorAction SilentlyContinue
+    }
+}
+
+function Read-ImapLine {
+    param([System.IO.Stream]$Stream)
+    $bytes = New-Object System.Collections.Generic.List[byte]
+    while ($true) {
+        $value = $Stream.ReadByte()
+        if ($value -lt 0) { throw 'IMAP connection closed' }
+        if ($value -eq 10) { break }
+        if ($value -ne 13) { $bytes.Add([byte]$value) }
+    }
+    return [System.Text.Encoding]::ASCII.GetString($bytes.ToArray())
+}
+
+function Read-ImapResponse {
+    param([System.IO.Stream]$Stream, [string]$Tag)
+    while ($true) {
+        $line = Read-ImapLine $Stream
+        if ($line.StartsWith("$Tag ")) {
+            if ($line -notmatch "^$Tag OK") { throw "IMAP command failed: $line" }
+            return
+        }
+    }
+}
+
+function ConvertTo-ImapQuoted {
+    param([string]$Value)
+    if ($Value -match "[\r\n]") { throw 'Invalid IMAP value' }
+    return '"' + $Value.Replace('\', '\').Replace('"', '\"') + '"'
+}
+
+# Appends a copy of an already-sent message to the Sent folder over IMAP.
+# Does nothing unless IMAP_HOST is configured. Callers treat failures as
+# non-fatal because the message itself has already been accepted by SMTP.
+function Save-SentCopy {
+    param($Settings, [System.Security.SecureString]$Password, [System.Net.Mail.MailMessage]$Message)
+    $imapHost = [string]$Settings['IMAP_HOST']
+    if (-not $imapHost) { return $false }
+    $port = 993
+    if ($Settings['IMAP_PORT'] -and -not [int]::TryParse($Settings['IMAP_PORT'], [ref]$port)) {
+        throw 'Invalid IMAP_PORT'
+    }
+    $folder = if ($Settings['IMAP_SENT_FOLDER']) { $Settings['IMAP_SENT_FOLDER'] } else { 'Sent' }
+    $mime = Get-MessageMimeBytes $Message
+    $tcp = New-Object System.Net.Sockets.TcpClient
+    $plain = $null
+    try {
+        $tcp.ReceiveTimeout = 20000
+        $tcp.SendTimeout = 20000
+        $tcp.Connect($imapHost, $port)
+        $ssl = New-Object System.Net.Security.SslStream($tcp.GetStream(), $false)
+        $ssl.ReadTimeout = 20000
+        $ssl.WriteTimeout = 20000
+        $ssl.AuthenticateAsClient($imapHost)
+        $send = {
+            param([string]$Text)
+            $data = [System.Text.Encoding]::UTF8.GetBytes($Text + "`r`n")
+            $ssl.Write($data, 0, $data.Length)
+            $ssl.Flush()
+        }
+        $null = Read-ImapLine $ssl
+        $plain = (New-Object System.Net.NetworkCredential('', $Password)).Password
+        & $send ('a1 LOGIN ' + (ConvertTo-ImapQuoted $Settings['SMTP_USER']) + ' ' + (ConvertTo-ImapQuoted $plain))
+        Read-ImapResponse $ssl 'a1'
+        & $send ('a2 APPEND ' + (ConvertTo-ImapQuoted $folder) + ' (\Seen) {' + $mime.Length + '}')
+        $line = Read-ImapLine $ssl
+        if (-not $line.StartsWith('+')) { throw "IMAP APPEND rejected: $line" }
+        $ssl.Write($mime, 0, $mime.Length)
+        $ssl.Write([byte[]](13, 10), 0, 2)
+        $ssl.Flush()
+        Read-ImapResponse $ssl 'a2'
+        & $send 'a3 LOGOUT'
+        return $true
+    }
+    finally {
+        $plain = $null
+        $tcp.Close()
+    }
+}
+
+function Save-SentCopySafely {
+    param($Settings, $Password, $Message)
+    try {
+        if (Save-SentCopy $Settings $Password $Message) { return 'Copy saved to Sent folder.' }
+        return $null
+    }
+    catch { return "Warning: could not save a Sent copy ($($_.Exception.Message))." }
+}

tools/send-approved-campaign-test.ps1

@@ -63,6 +63,7 @@ try {
     $client.Send($message)
     Write-CampaignAudit $db 'approved_campaign_test_accepted' ([string]$CampaignId) ("Internal test to $testTo")
     Write-Output "Approved campaign $CampaignId test accepted for $testTo. Live delivery counts did not advance."
+    if ($Send) { $sentNote = Save-SentCopySafely $settings $password $message; if ($sentNote) { Write-Output $sentNote } }
 }
 finally {
     if ($client) { $client.Dispose() }

tools/send-campaign-test.ps1

@@ -58,6 +58,7 @@ try {
     $client.Send($message)
     Write-CampaignAudit $db 'campaign_test_accepted' $review.Token ("Internal test to $($review.Identity.TestTo)")
     Write-Output "Campaign test accepted for $($review.Identity.TestTo). Check the received message before approval."
+    if ($Send) { $sentNote = Save-SentCopySafely $settings $password $message; if ($sentNote) { Write-Output $sentNote } }
 }
 finally {
     if ($client) { $client.Dispose() }