diff --git a/services/galley/src/Galley/API/Error.hs b/services/galley/src/Galley/API/Error.hs
index f6728a7d68..6a1c4d7c97 100644
--- a/services/galley/src/Galley/API/Error.hs
+++ b/services/galley/src/Galley/API/Error.hs
@@ -99,8 +99,8 @@ badConvState cid =
     "Connect conversation with more than 2 members: "
       <> LT.pack (show cid)
 
-legalHoldServiceUnavailable :: Wai.Error
-legalHoldServiceUnavailable = Wai.mkError status412 "legalhold-unavailable" "legal hold service does not respond or tls handshake could not be completed (did you pin the wrong public key?)"
+legalHoldServiceUnavailable :: Show a => a -> Wai.Error
+legalHoldServiceUnavailable e = Wai.mkError status412 "legalhold-unavailable" ("legal hold service unavailable with underlying error: " <> (LT.pack . show $ e))
 
 invalidTeamNotificationId :: Wai.Error
 invalidTeamNotificationId = Wai.mkError status400 "invalid-notification-id" "Could not parse notification id (must be UUIDv1)."
diff --git a/services/galley/src/Galley/External/LegalHoldService/Internal.hs b/services/galley/src/Galley/External/LegalHoldService/Internal.hs
index a26e5212bd..2106138763 100644
--- a/services/galley/src/Galley/External/LegalHoldService/Internal.hs
+++ b/services/galley/src/Galley/External/LegalHoldService/Internal.hs
@@ -55,7 +55,7 @@ makeVerifiedRequestWithManager mgr (HttpsUrl url) reqBuilder = do
         . prependPath (uriPath url)
     errHandler e = do
       Log.info . Log.msg $ "error making request to legalhold service: " <> show e
-      throwM legalHoldServiceUnavailable
+      throwM (legalHoldServiceUnavailable e)
     prependPath :: ByteString -> Http.Request -> Http.Request
     prependPath pth req = req {Http.path = pth </> Http.path req}
     -- append two paths with exactly one slash