diff --git a/pkg/middleware/auth_proxy.go b/pkg/middleware/auth_proxy.go
index 890fd5e4f24..9ec5852b73d 100644
--- a/pkg/middleware/auth_proxy.go
+++ b/pkg/middleware/auth_proxy.go
@@ -31,6 +31,7 @@ func initContextWithAuthProxy(store *remotecache.RemoteCache, ctx *m.ReqContext,
 
 	// Check if allowed to continue with this IP
 	if result, err := auth.IsAllowedIP(); !result {
+		ctx.Logger.Error("auth proxy: failed to check whitelisted ip addresses", "message", err.Error(), "error", err.DetailsError)
 		ctx.Handle(407, err.Error(), err.DetailsError)
 		return true
 	}
@@ -38,6 +39,7 @@ func initContextWithAuthProxy(store *remotecache.RemoteCache, ctx *m.ReqContext,
 	// Try to log in user from various providers
 	id, err := auth.Login()
 	if err != nil {
+		ctx.Logger.Error("auth proxy: failed to login", "message", err.Error(), "error", err.DetailsError)
 		ctx.Handle(500, err.Error(), err.DetailsError)
 		return true
 	}
@@ -45,6 +47,7 @@ func initContextWithAuthProxy(store *remotecache.RemoteCache, ctx *m.ReqContext,
 	// Get full user info
 	user, err := auth.GetSignedUser(id)
 	if err != nil {
+		ctx.Logger.Error("auth proxy: failed to get signed in user", "message", err.Error(), "error", err.DetailsError)
 		ctx.Handle(500, err.Error(), err.DetailsError)
 		return true
 	}
@@ -55,6 +58,7 @@ func initContextWithAuthProxy(store *remotecache.RemoteCache, ctx *m.ReqContext,
 
 	// Remember user data it in cache
 	if err := auth.Remember(id); err != nil {
+		ctx.Logger.Error("auth proxy: failed to store user in cache", "message", err.Error(), "error", err.DetailsError)
 		ctx.Handle(500, err.Error(), err.DetailsError)
 		return true
 	}