t-265.5: Add SMTP email sending for Ava outreach

- Add emailSendTool to Email.hs for sending approved drafts
- Add sendApprovedEmail function that checks draft status
- Use Network.Mail.Mime.simpleMail' with SMTP.sendMail
- Integrate with Outreach module to verify approval and mark sent
- Add tests for new tool

1 files changed, 116 insertions, 5 deletions

diff --git a/Omni/Agent/Tools/Email.hs b/Omni/Agent/Tools/Email.hs
index 9c63340..7a9bc64 100644
--- a/Omni/Agent/Tools/Email.hs
+++ b/Omni/Agent/Tools/Email.hs
@@ -3,14 +3,15 @@
 {-# LANGUAGE ScopedTypeVariables #-}
 {-# LANGUAGE NoImplicitPrelude #-}
 
--- | Email tools for IMAP access via Telegram bot.
+-- | Email tools for IMAP and SMTP access via Telegram bot.
 --
 -- Provides email management for agents:
 -- - Check for urgent/time-sensitive emails
 -- - Identify emails needing response vs FYI
 -- - Auto-unsubscribe from marketing
+-- - Send approved outreach emails via SMTP
 --
--- Uses HaskellNet for proper IMAP client support.
+-- Uses HaskellNet for IMAP/SMTP client support.
 -- Password retrieved via `pass ben@bensima.com`.
 --
 -- : out omni-agent-tools-email
@@ -26,6 +27,7 @@ module Omni.Agent.Tools.Email
     emailReadTool,
     emailUnsubscribeTool,
     emailArchiveTool,
+    emailSendTool,
 
     -- * All tools
     allEmailTools,
@@ -36,6 +38,7 @@ module Omni.Agent.Tools.Email
     unsubscribeFromEmail,
     archiveEmail,
     getPassword,
+    sendApprovedEmail,
 
     -- * Scheduled Check
     emailCheckLoop,
@@ -54,6 +57,7 @@ import qualified Data.Aeson.KeyMap as KeyMap
 import qualified Data.ByteString.Char8 as BS8
 import qualified Data.List as List
 import qualified Data.Text as Text
+import qualified Data.Text.Lazy as LText
 import Data.Time (NominalDiffTime, UTCTime, addUTCTime, getCurrentTime)
 import Data.Time.Format (defaultTimeLocale, formatTime, parseTimeM)
 import Data.Time.LocalTime (TimeZone (..), utcToZonedTime)
@@ -61,7 +65,11 @@ import qualified Network.HTTP.Simple as HTTP
 import qualified Network.HaskellNet.IMAP as IMAP
 import Network.HaskellNet.IMAP.Connection (IMAPConnection)
 import qualified Network.HaskellNet.IMAP.SSL as IMAPSSL
+import qualified Network.HaskellNet.SMTP as SMTP
+import qualified Network.HaskellNet.SMTP.SSL as SMTPSSL
+import Network.Mail.Mime (Address (..), simpleMail')
 import qualified Omni.Agent.Engine as Engine
+import qualified Omni.Agent.Tools.Outreach as Outreach
 import qualified Omni.Test as Test
 import System.Process (readProcessWithExitCode)
 import Text.Regex.Applicative (RE, anySym, few, (=~))
@@ -82,8 +90,10 @@ test =
         Engine.toolName emailUnsubscribeTool Test.@=? "email_unsubscribe",
       Test.unit "emailArchiveTool has correct name" <| do
         Engine.toolName emailArchiveTool Test.@=? "email_archive",
-      Test.unit "allEmailTools has 4 tools" <| do
-        length allEmailTools Test.@=? 4,
+      Test.unit "emailSendTool has correct name" <| do
+        Engine.toolName emailSendTool Test.@=? "email_send",
+      Test.unit "allEmailTools has 5 tools" <| do
+        length allEmailTools Test.@=? 5,
       Test.unit "parseEmailHeaders extracts fields" <| do
         let headers =
               "From: test@example.com\r\n\
@@ -314,7 +324,8 @@ allEmailTools =
   [ emailCheckTool,
     emailReadTool,
     emailUnsubscribeTool,
-    emailArchiveTool
+    emailArchiveTool,
+    emailSendTool
   ]
 
 emailCheckTool :: Engine.Tool
@@ -562,3 +573,103 @@ performScheduledCheck sendFn chatId = do
     formatOne :: EmailSummary -> Text
     formatOne e =
       "• " <> emailSubject e <> " (from: " <> emailFrom e <> ", uid: " <> tshow (emailUid e) <> ")"
+
+smtpServer :: String
+smtpServer = "bensima.com"
+
+smtpUser :: String
+smtpUser = "ben@bensima.com"
+
+withSmtpConnection :: (SMTP.SMTPConnection -> IO a) -> IO (Either Text a)
+withSmtpConnection action = do
+  pwResult <- getPassword
+  case pwResult of
+    Left err -> pure (Left err)
+    Right pw -> do
+      result <-
+        try <| do
+          conn <- SMTPSSL.connectSMTPSSL smtpServer
+          authSuccess <- SMTP.authenticate SMTP.LOGIN smtpUser (Text.unpack pw) conn
+          if authSuccess
+            then do
+              r <- action conn
+              SMTP.closeSMTP conn
+              pure r
+            else do
+              SMTP.closeSMTP conn
+              panic "SMTP authentication failed"
+      case result of
+        Left (e :: SomeException) -> pure (Left ("SMTP error: " <> tshow e))
+        Right r -> pure (Right r)
+
+sendApprovedEmail :: Text -> IO (Either Text Text)
+sendApprovedEmail draftId = do
+  mDraft <- Outreach.getDraft draftId
+  case mDraft of
+    Nothing -> pure (Left "Draft not found")
+    Just draft -> do
+      case Outreach.draftStatus draft of
+        Outreach.Approved -> do
+          let recipientAddr = Address Nothing (Outreach.draftRecipient draft)
+              senderAddr = Address (Just "Ben Sima") "ben@bensima.com"
+              subject = fromMaybe "" (Outreach.draftSubject draft)
+              body = LText.fromStrict (Outreach.draftBody draft)
+              footer = "\n\n---\nSent by Ava on behalf of Ben"
+              fullBody = body <> footer
+              mail = simpleMail' recipientAddr senderAddr subject fullBody
+          sendResult <-
+            withSmtpConnection <| \conn -> do
+              SMTP.sendMail mail conn
+          case sendResult of
+            Left err -> pure (Left err)
+            Right () -> do
+              _ <- Outreach.markSent draftId
+              pure (Right ("Email sent to " <> Outreach.draftRecipient draft))
+        Outreach.Pending -> pure (Left "Draft is still pending approval")
+        Outreach.Rejected -> pure (Left "Draft was rejected")
+        Outreach.Sent -> pure (Left "Draft was already sent")
+
+emailSendTool :: Engine.Tool
+emailSendTool =
+  Engine.Tool
+    { Engine.toolName = "email_send",
+      Engine.toolDescription =
+        "Send an approved outreach email. Only sends emails that have been approved "
+          <> "by Ben in the outreach queue. Use outreach_draft to create drafts first, "
+          <> "wait for approval, then use this to send.",
+      Engine.toolJsonSchema =
+        Aeson.object
+          [ "type" .= ("object" :: Text),
+            "properties"
+              .= Aeson.object
+                [ "draft_id"
+                    .= Aeson.object
+                      [ "type" .= ("string" :: Text),
+                        "description" .= ("ID of the approved draft to send" :: Text)
+                      ]
+                ],
+            "required" .= (["draft_id"] :: [Text])
+          ],
+      Engine.toolExecute = executeEmailSend
+    }
+
+executeEmailSend :: Aeson.Value -> IO Aeson.Value
+executeEmailSend v = do
+  let draftIdM = case v of
+        Aeson.Object obj -> case KeyMap.lookup "draft_id" obj of
+          Just (Aeson.String s) -> Just s
+          _ -> Nothing
+        _ -> Nothing
+  case draftIdM of
+    Nothing -> pure (Aeson.object ["error" .= ("Missing draft_id parameter" :: Text)])
+    Just draftId -> do
+      result <- sendApprovedEmail draftId
+      case result of
+        Left err -> pure (Aeson.object ["error" .= err])
+        Right msg ->
+          pure
+            ( Aeson.object
+                [ "success" .= True,
+                  "message" .= msg
+                ]
+            )