diff --git a/include/CLI/App.hpp b/include/CLI/App.hpp
index 206473f6..861c901b 100644
--- a/include/CLI/App.hpp
+++ b/include/CLI/App.hpp
@@ -1146,6 +1146,10 @@ class App {
         for(const Option_p &opt : options_) {
             // Required or partially filled
             if(opt->get_required() || opt->count() != 0) {
+                // Make sure enough -N arguments parsed (+N is already handled in parsing function)
+                if(opt->get_expected() < 0 && opt->count() < static_cast<size_t>(-opt->get_expected()))
+                    throw ArgumentMismatch(opt->single_name() + ": At least " + std::to_string(-opt->get_expected()) +
+                                           " required");
 
                 // Required but empty
                 if(opt->get_required() && opt->count() == 0)
@@ -1408,8 +1412,6 @@ class App {
                 args.pop_back();
                 collected++;
             }
-            if(op->results_.size() < static_cast<size_t>(-num))
-                throw ArgumentMismatch(op->single_name() + ": At least " + std::to_string(-num) + " required");
 
         } else {
             while(num > 0 && !args.empty()) {
diff --git a/tests/AppTest.cpp b/tests/AppTest.cpp
index 2ffce3d4..d171c6ed 100644
--- a/tests/AppTest.cpp
+++ b/tests/AppTest.cpp
@@ -324,10 +324,33 @@ TEST_F(TApp, RequiredOptsDoubleShort) {
 
     EXPECT_THROW(run(), CLI::ArgumentMismatch);
 
+    app.reset();
+
+    args = {"-s", "one", "-s", "one", "-s", "one"};
+
+    EXPECT_THROW(run(), CLI::ArgumentMismatch);
+}
+
+TEST_F(TApp, RequiredOptsDoubleNeg) {
+    std::vector<std::string> strs;
+    app.add_option("-s", strs)->required()->expected(-2);
+
+    args = {"-s", "one"};
+
+    EXPECT_THROW(run(), CLI::ArgumentMismatch);
+
+    app.reset();
+
+    args = {"-s", "one", "two", "-s", "three"};
+
+    EXPECT_NO_THROW(run());
+
+    EXPECT_EQ(strs, std::vector<std::string>({"one", "two", "three"}));
+
     app.reset();
     args = {"-s", "one", "two"};
 
-    run();
+    EXPECT_NO_THROW(run());
 
     EXPECT_EQ(strs, std::vector<std::string>({"one", "two"}));
 }