bullet proof smtp

changelog.d/2-features/smtp-logging

@@ -0,0 +1 @@
+Add more logs to SMTP mail sending. Ensure that logs are written before the application fails due to SMTP misconfiguration.

libs/types-common/default.nix

@@ -32,6 +32,7 @@
 , lens-datetime
 , lib
 , mime
+, network
 , optparse-applicative
 , pem
 , protobuf
@@ -91,6 +92,7 @@ mkDerivation {
     lens
     lens-datetime
     mime
+    network
     optparse-applicative
     pem
     protobuf

libs/types-common/src/Wire/Arbitrary.hs

@@ -42,9 +42,10 @@ import GHC.Generics (Rep)
 import Generic.Random (listOf', (:+) ((:+)))
 import qualified Generic.Random as Generic
 import Imports
+import Network.Socket (PortNumber)
 import Test.QuickCheck.Arbitrary (Arbitrary (arbitrary))
 import qualified Test.QuickCheck.Arbitrary as QC
-import Test.QuickCheck.Gen (Gen (MkGen))
+import Test.QuickCheck.Gen (Gen (MkGen), chooseBoundedIntegral)
 import Test.QuickCheck.Instances ()
 import Test.QuickCheck.Random
 
@@ -120,3 +121,6 @@ generateExample :: Arbitrary a => a
 generateExample =
   let (MkGen f) = arbitrary
    in f (mkQCGen 42) 42
+
+instance Arbitrary PortNumber where
+  arbitrary = chooseBoundedIntegral (minBound :: PortNumber, maxBound :: PortNumber)

libs/types-common/types-common.cabal

@@ -113,6 +113,7 @@ library
     , lens                   >=4.10
     , lens-datetime          >=0.3
     , mime                   >=0.4.0.2
+    , network
     , optparse-applicative   >=0.10
     , pem
     , protobuf               >=0.2

nix/haskell-pins.nix

@@ -203,6 +203,14 @@ let
         tasty-hunit = "hunit";
       };
     };
+    # This can be removed once postie 0.6.0.3 (or later) is in nixpkgs
+    postie = {
+      src = fetchgit {
+        url = "https://github.com/alexbiehl/postie.git";
+        rev = "c92702386f760fcaa65cd052dc8114889c001e3f";
+        sha256 = "sha256-yiw6hg3guRWS6CVdrUY8wyIDxoqfGjIVMrEtP+Fys0Y=";
+      };
+    };
   };
   hackagePins = {
     kind-generics = {

nix/manual-overrides.nix

@@ -58,4 +58,7 @@ hself: hsuper: {
 
   # Make hoogle static to reduce size of the hoogle image
   hoogle = hlib.justStaticExecutables hsuper.hoogle;
+
+  # Postie has been fixed upstream (master)
+  postie = hlib.markUnbroken (hlib.doJailbreak hsuper.postie);
 }

services/brig/brig.cabal

@@ -287,6 +287,8 @@ library
     , text                       >=0.11
     , text-icu-translit          >=0.1
     , time                       >=1.1
+    , time-out
+    , time-units
     , tinylog                    >=0.10
     , transformers               >=0.3
     , types-common               >=0.16
@@ -463,6 +465,7 @@ executable brig-integration
     Federation.Util
     Index.Create
     Main
+    SMTP
     Util
     Util.AWS
 
@@ -552,13 +555,16 @@ executable brig-integration
     , lens-aeson
     , metrics-wai
     , mime                   >=0.4
+    , mime-mail
     , MonadRandom            >=0.5
     , mtl
     , network
     , optparse-applicative
     , pem
+    , pipes
     , polysemy
     , polysemy-wire-zoo
+    , postie                 >=0.6.0.3
     , process
     , proto-lens
     , QuickCheck
@@ -579,6 +585,7 @@ executable brig-integration
     , temporary              >=1.2.1
     , text
     , time                   >=1.5
+    , time-units
     , tinylog
     , transformers
     , types-common           >=0.3

services/brig/default.nix

@@ -85,9 +85,11 @@
 , network-conduit-tls
 , optparse-applicative
 , pem
+, pipes
 , polysemy
 , polysemy-plugin
 , polysemy-wire-zoo
+, postie
 , process
 , proto-lens
 , QuickCheck
@@ -130,6 +132,8 @@
 , text
 , text-icu-translit
 , time
+, time-out
+, time-units
 , tinylog
 , transformers
 , types-common
@@ -267,6 +271,8 @@ mkDerivation {
     text
     text-icu-translit
     time
+    time-out
+    time-units
     tinylog
     transformers
     types-common
@@ -329,13 +335,16 @@ mkDerivation {
     lens-aeson
     metrics-wai
     mime
+    mime-mail
     MonadRandom
     mtl
     network
     optparse-applicative
     pem
+    pipes
     polysemy
     polysemy-wire-zoo
+    postie
     process
     proto-lens
     QuickCheck
@@ -356,6 +365,7 @@ mkDerivation {
     temporary
     text
     time
+    time-units
     tinylog
     transformers
     types-common

services/brig/src/Brig/Email.hs

@@ -40,19 +40,20 @@ module Brig.Email
 where
 
 import qualified Brig.AWS as AWS
-import Brig.App (Env, awsEnv, smtpEnv)
+import Brig.App (Env, applog, awsEnv, smtpEnv)
 import qualified Brig.SMTP as SMTP
 import Control.Lens (view)
+import Control.Monad.Catch
 import qualified Data.Text as Text
 import Imports
 import Network.Mail.Mime
 import Wire.API.User
 
 -------------------------------------------------------------------------------
-sendMail :: (MonadIO m, MonadReader Env m) => Mail -> m ()
+sendMail :: (MonadIO m, MonadCatch m, MonadReader Env m) => Mail -> m ()
 sendMail m =
   view smtpEnv >>= \case
-    Just smtp -> SMTP.sendMail smtp m
+    Just smtp -> view applog >>= \logger -> SMTP.sendMail logger smtp m
     Nothing -> view awsEnv >>= \e -> AWS.execute e $ AWS.sendMail m
 
 -------------------------------------------------------------------------------