diff --git a/app/file.go b/app/file.go
index 3dc20d4f37..056c70fe0e 100644
--- a/app/file.go
+++ b/app/file.go
@@ -647,6 +647,11 @@ func (a *App) UploadFileX(channelId, name string, input io.Reader,
 func (t *uploadFileTask) readAll() *model.AppError {
 	_, err := t.buf.ReadFrom(t.limitedInput)
 	if err != nil {
+		// Ugly hack: the error is not exported from net/http.
+		if err.Error() == "http: request body too large" {
+			return t.newAppError("api.file.upload_file.too_large_detailed.app_error",
+				"", http.StatusRequestEntityTooLarge, "Length", t.buf.Len(), "Limit", t.limit)
+		}
 		return t.newAppError("api.file.upload_file.read_request.app_error",
 			err.Error(), http.StatusBadRequest)
 	}
diff --git a/web/handlers.go b/web/handlers.go
index ac650836fc..59a396f7ec 100644
--- a/web/handlers.go
+++ b/web/handlers.go
@@ -4,6 +4,7 @@
 package web
 
 import (
+	"bytes"
 	"fmt"
 	"net/http"
 	"reflect"
@@ -90,6 +91,14 @@ func (h Handler) ServeHTTP(w http.ResponseWriter, r *http.Request) {
 	c.App.Path = r.URL.Path
 	c.Log = c.App.Log
 
+	// Set the max request body size to be equal to MaxFileSize.
+	// Ideally, non-file request bodies should be smaller than file request bodies,
+	// but we don't have a clean way to identify all file upload handlers.
+	// So to keep it simple, we clamp it to the max file size.
+	// We add a buffer of bytes.MinRead so that file sizes close to max file size
+	// do not get cut off.
+	r.Body = http.MaxBytesReader(w, r.Body, *c.App.Config().FileSettings.MaxFileSize+bytes.MinRead)
+
 	subpath, _ := utils.GetSubpathFromConfig(c.App.Config())
 	siteURLHeader := app.GetProtocol(r) + "://" + r.Host + subpath
 	c.SetSiteURLHeader(siteURLHeader)