diff --git a/CHANGELOG.md b/CHANGELOG.md
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,4 +1,11 @@
-## [_Unreleased_](https://github.com/freckle/freckle-app/compare/v1.10.5.1...main)
+## [_Unreleased_](https://github.com/freckle/freckle-app/compare/v1.10.6.0...main)
+
+## [v1.10.6.0](https://github.com/freckle/freckle-app/compare/v1.10.5.0...v1.10.6.0)
+
+- The Bugsnag settings created by `envParseBugsnagSettings` now has a `BeforeNotify`
+  that appropriately handles `AnnotatedException`. Its special handling of `SqlError`
+  and `HttpException` now works in the presence of annotations. If a `CallStack`
+  annotation is present, that will be used as the stacktrace for reported events.
 
 ## [v1.10.5.1](https://github.com/freckle/freckle-app/compare/v1.10.5.0...v1.10.5.1)
 
diff --git a/freckle-app.cabal b/freckle-app.cabal
--- a/freckle-app.cabal
+++ b/freckle-app.cabal
@@ -1,6 +1,6 @@
 cabal-version:      1.18
 name:               freckle-app
-version:            1.10.5.1
+version:            1.10.6.0
 license:            MIT
 license-file:       LICENSE
 maintainer:         Freckle Education
@@ -26,7 +26,10 @@
         Freckle.App.Aeson
         Freckle.App.Async
         Freckle.App.Bugsnag
+        Freckle.App.Bugsnag.CallStack
+        Freckle.App.Bugsnag.HttpException
         Freckle.App.Bugsnag.MetaData
+        Freckle.App.Bugsnag.SqlError
         Freckle.App.Csv
         Freckle.App.Database
         Freckle.App.Database.XRay
diff --git a/library/Freckle/App/Bugsnag.hs b/library/Freckle/App/Bugsnag.hs
--- a/library/Freckle/App/Bugsnag.hs
+++ b/library/Freckle/App/Bugsnag.hs
@@ -11,9 +11,6 @@
     -- * Loading settings
   , envParseBugsnagSettings
 
-    -- * Exported for testing
-  , sqlErrorGroupingHash
-
     -- * Re-exports
   , MonadReader
   , runReaderT
@@ -22,22 +19,21 @@
 
 import Freckle.App.Prelude
 
+import qualified Control.Exception as Base (Exception)
 import Control.Lens (Lens', view)
 import Control.Monad.Catch (MonadMask)
 import Control.Monad.Reader (runReaderT)
-import Data.Bugsnag
-import Data.Bugsnag.Settings
-import qualified Data.ByteString.Char8 as BS8
+import Data.Bugsnag (App (..), Event (..), defaultApp)
+import Data.Bugsnag.Settings (Settings (..), defaultSettings)
 import Data.List (isInfixOf)
-import Database.PostgreSQL.Simple (SqlError (..))
-import Database.PostgreSQL.Simple.Errors
 import Freckle.App.Async (async)
+import Freckle.App.Bugsnag.CallStack (callStackBeforeNotify)
+import Freckle.App.Bugsnag.HttpException (httpExceptionBeforeNotify)
+import Freckle.App.Bugsnag.SqlError (sqlErrorBeforeNotify)
 import qualified Freckle.App.Env as Env
-import qualified Freckle.App.Exception.MonadUnliftIO as Exception
 import Network.Bugsnag hiding (notifyBugsnag, notifyBugsnagWith)
 import qualified Network.Bugsnag as Bugsnag
-import Network.HTTP.Client (HttpException (..), host, method)
-import Yesod.Core.Lens
+import Yesod.Core.Lens (envL, siteL)
 import Yesod.Core.Types (HandlerData)
 
 class HasAppVersion env where
@@ -72,7 +68,7 @@
      , MonadUnliftIO m
      , MonadReader env m
      , HasBugsnagSettings env
-     , Exception.Exception e
+     , Base.Exception e
      )
   => e
   -> m ()
@@ -84,7 +80,7 @@
      , MonadUnliftIO m
      , MonadReader env m
      , HasBugsnagSettings env
-     , Exception.Exception e
+     , Base.Exception e
      )
   => BeforeNotify
   -> e
@@ -93,54 +89,6 @@
   settings <- view bugsnagSettingsL
   void $ async $ liftIO $ Bugsnag.notifyBugsnagWith f settings ex
 
-asSqlError :: SqlError -> BeforeNotify
-asSqlError err@SqlError {..} = toSqlGrouping <> toSqlException
- where
-  toSqlGrouping = maybe mempty setGroupingHash (sqlErrorGroupingHash err)
-  toSqlException = updateExceptions $ \ex ->
-    ex
-      { exception_errorClass = decodeUtf8 $ "SqlError-" <> sqlState
-      , exception_message =
-          Just $
-            decodeUtf8 $
-              sqlErrorMsg
-                <> ": "
-                <> sqlErrorDetail
-                <> " ("
-                <> sqlErrorHint
-                <> ")"
-      }
-
-sqlErrorGroupingHash :: SqlError -> Maybe Text
-sqlErrorGroupingHash err = do
-  violation <- constraintViolation err
-  decodeUtf8 <$> case violation of
-    ForeignKeyViolation table constraint -> pure $ table <> "." <> constraint
-    UniqueViolation constraint -> pure constraint
-    _ -> Nothing
-
-asHttpException :: HttpException -> BeforeNotify
-asHttpException (HttpExceptionRequest req content) =
-  setGroupingHash (decodeUtf8 $ host req) <> update
- where
-  update = updateExceptions $ \ex ->
-    ex
-      { exception_errorClass = "HttpExceptionRequest"
-      , exception_message =
-          Just
-            . decodeUtf8
-            $ method req
-              <> " request to "
-              <> host req
-              <> " failed: "
-              <> BS8.pack (show content)
-      }
-asHttpException (InvalidUrlException url msg) = updateExceptions $ \ex ->
-  ex
-    { exception_errorClass = "InvalidUrlException"
-    , exception_message = Just $ pack $ url <> " is invalid: " <> msg
-    }
-
 -- | Set StackFrame's InProject to @'False'@ for Error Helper modules
 --
 -- We want exceptions grouped by the the first stack-frame that is /not/ them.
@@ -148,8 +96,6 @@
 maskErrorHelpers :: BeforeNotify
 maskErrorHelpers = setStackFramesInProjectByFile (`isInfixOf` "Exceptions")
 
--- brittany-disable-next-binding
-
 envParseBugsnagSettings :: Env.Parser Env.Error Settings
 envParseBugsnagSettings =
   build
@@ -164,6 +110,7 @@
 
 globalBeforeNotify :: BeforeNotify
 globalBeforeNotify =
-  updateEventFromOriginalException asSqlError
-    <> updateEventFromOriginalException asHttpException
+  callStackBeforeNotify
+    <> sqlErrorBeforeNotify
+    <> httpExceptionBeforeNotify
     <> maskErrorHelpers
diff --git a/library/Freckle/App/Bugsnag/CallStack.hs b/library/Freckle/App/Bugsnag/CallStack.hs
new file mode 100644
--- /dev/null
+++ b/library/Freckle/App/Bugsnag/CallStack.hs
@@ -0,0 +1,46 @@
+module Freckle.App.Bugsnag.CallStack
+  ( callStackBeforeNotify
+  , attachCallStack
+  , callStackToStackFrames
+  , callSiteToStackFrame
+
+    -- * Re-exports
+  , CallStack
+  , SrcLoc
+  , StackFrame
+  ) where
+
+import Freckle.App.Prelude
+
+import Control.Exception.Annotated (annotatedExceptionCallStack)
+import Data.Bugsnag (Exception (..), StackFrame (..), defaultStackFrame)
+import qualified Data.Text as T
+import Freckle.App.Exception.Types (AnnotatedException)
+import GHC.Stack (CallStack, SrcLoc (..), getCallStack)
+import Network.Bugsnag (BeforeNotify, updateExceptions)
+import Network.Bugsnag.BeforeNotify (updateEventFromOriginalException)
+
+-- | Copy the call stack from an AnnotatedException
+callStackBeforeNotify :: BeforeNotify
+callStackBeforeNotify =
+  updateEventFromOriginalException @(AnnotatedException SomeException) $ \e ->
+    foldMap attachCallStack $ annotatedExceptionCallStack e
+
+attachCallStack :: CallStack -> BeforeNotify
+attachCallStack cs =
+  updateExceptions $ \ex ->
+    ex {exception_stacktrace = callStackToStackFrames cs}
+
+-- | Converts a GHC call stack to a list of stack frames suitable
+--   for use as the stacktrace in a Bugsnag exception
+callStackToStackFrames :: CallStack -> [StackFrame]
+callStackToStackFrames = fmap callSiteToStackFrame . getCallStack
+
+callSiteToStackFrame :: (String, SrcLoc) -> StackFrame
+callSiteToStackFrame (str, loc) =
+  defaultStackFrame
+    { stackFrame_method = T.pack str
+    , stackFrame_file = T.pack $ srcLocFile loc
+    , stackFrame_lineNumber = srcLocStartLine loc
+    , stackFrame_columnNumber = Just $ srcLocStartCol loc
+    }
diff --git a/library/Freckle/App/Bugsnag/HttpException.hs b/library/Freckle/App/Bugsnag/HttpException.hs
new file mode 100644
--- /dev/null
+++ b/library/Freckle/App/Bugsnag/HttpException.hs
@@ -0,0 +1,47 @@
+module Freckle.App.Bugsnag.HttpException
+  ( httpExceptionBeforeNotify
+
+    -- * Re-exports
+  , HttpException
+  ) where
+
+import Freckle.App.Prelude
+
+import Data.Bugsnag (Exception (..))
+import qualified Data.ByteString.Char8 as BS8
+import Freckle.App.Exception.Types (AnnotatedException)
+import qualified Freckle.App.Exception.Types as Annotated
+import Network.Bugsnag
+  ( BeforeNotify
+  , setGroupingHash
+  , updateEventFromOriginalException
+  , updateExceptions
+  )
+import Network.HTTP.Client (HttpException (..), host, method)
+
+httpExceptionBeforeNotify :: BeforeNotify
+httpExceptionBeforeNotify =
+  updateEventFromOriginalException @(AnnotatedException HttpException)
+    (asHttpException . Annotated.exception)
+
+asHttpException :: HttpException -> BeforeNotify
+asHttpException (HttpExceptionRequest req content) =
+  setGroupingHash (decodeUtf8 $ host req) <> update
+ where
+  update = updateExceptions $ \ex ->
+    ex
+      { exception_errorClass = "HttpExceptionRequest"
+      , exception_message =
+          Just
+            . decodeUtf8
+            $ method req
+              <> " request to "
+              <> host req
+              <> " failed: "
+              <> BS8.pack (show content)
+      }
+asHttpException (InvalidUrlException url msg) = updateExceptions $ \ex ->
+  ex
+    { exception_errorClass = "InvalidUrlException"
+    , exception_message = Just $ pack $ url <> " is invalid: " <> msg
+    }
diff --git a/library/Freckle/App/Bugsnag/MetaData.hs b/library/Freckle/App/Bugsnag/MetaData.hs
--- a/library/Freckle/App/Bugsnag/MetaData.hs
+++ b/library/Freckle/App/Bugsnag/MetaData.hs
@@ -17,11 +17,11 @@
 
 import Blammo.Logging (Pair, myThreadContext)
 import Control.Lens (Lens', lens, to, view, (<>~))
-import Data.Aeson
+import Data.Aeson (KeyValue ((.=)), Object, Value (..), object)
 import Data.Bugsnag (Event (..))
 import Data.String (fromString)
 import qualified Freckle.App.Aeson as Aeson
-import Freckle.App.Bugsnag
+import Freckle.App.Bugsnag (BeforeNotify, updateEvent)
 import Freckle.App.Stats (HasStatsClient (..), tagsL)
 
 newtype MetaData = MetaData
diff --git a/library/Freckle/App/Bugsnag/SqlError.hs b/library/Freckle/App/Bugsnag/SqlError.hs
new file mode 100644
--- /dev/null
+++ b/library/Freckle/App/Bugsnag/SqlError.hs
@@ -0,0 +1,57 @@
+module Freckle.App.Bugsnag.SqlError
+  ( sqlErrorBeforeNotify
+
+    -- * Re-exports
+  , SqlError
+
+    -- * Exported for testing
+  , sqlErrorGroupingHash
+  ) where
+
+import Freckle.App.Prelude
+
+import Data.Bugsnag (Exception (..))
+import Database.PostgreSQL.Simple (SqlError (..))
+import Database.PostgreSQL.Simple.Errors
+  ( ConstraintViolation (..)
+  , constraintViolation
+  )
+import Freckle.App.Exception.Types (AnnotatedException)
+import qualified Freckle.App.Exception.Types as Annotated
+import Network.Bugsnag
+  ( BeforeNotify
+  , setGroupingHash
+  , updateEventFromOriginalException
+  , updateExceptions
+  )
+
+sqlErrorBeforeNotify :: BeforeNotify
+sqlErrorBeforeNotify =
+  updateEventFromOriginalException @(AnnotatedException SqlError)
+    (asSqlError . Annotated.exception)
+
+asSqlError :: SqlError -> BeforeNotify
+asSqlError err@SqlError {..} = toSqlGrouping <> toSqlException
+ where
+  toSqlGrouping = maybe mempty setGroupingHash (sqlErrorGroupingHash err)
+  toSqlException = updateExceptions $ \ex ->
+    ex
+      { exception_errorClass = decodeUtf8 $ "SqlError-" <> sqlState
+      , exception_message =
+          Just $
+            decodeUtf8 $
+              sqlErrorMsg
+                <> ": "
+                <> sqlErrorDetail
+                <> " ("
+                <> sqlErrorHint
+                <> ")"
+      }
+
+sqlErrorGroupingHash :: SqlError -> Maybe Text
+sqlErrorGroupingHash err = do
+  violation <- constraintViolation err
+  decodeUtf8 <$> case violation of
+    ForeignKeyViolation table constraint -> pure $ table <> "." <> constraint
+    UniqueViolation constraint -> pure constraint
+    _ -> Nothing
diff --git a/package.yaml b/package.yaml
--- a/package.yaml
+++ b/package.yaml
@@ -1,5 +1,5 @@
 name: freckle-app
-version: 1.10.5.1
+version: 1.10.6.0
 maintainer: Freckle Education
 category: Utils
 github: freckle/freckle-app
diff --git a/tests/Freckle/App/BugsnagSpec.hs b/tests/Freckle/App/BugsnagSpec.hs
--- a/tests/Freckle/App/BugsnagSpec.hs
+++ b/tests/Freckle/App/BugsnagSpec.hs
@@ -6,7 +6,7 @@
 
 import Data.ByteString (ByteString)
 import Database.PostgreSQL.Simple (ExecStatus (..), SqlError (..))
-import Freckle.App.Bugsnag
+import Freckle.App.Bugsnag.SqlError (sqlErrorGroupingHash)
 import Test.Hspec
 
 spec :: Spec