diff --git a/fuzz/fuzzApp.cpp b/fuzz/fuzzApp.cpp
index 7aae17ae..9d050eae 100644
--- a/fuzz/fuzzApp.cpp
+++ b/fuzz/fuzzApp.cpp
@@ -193,7 +193,18 @@ bool FuzzApp::compare(const FuzzApp &other) const {
     }
 
     if(vv1 != other.vv1) {
-        return false;
+        if(vv1.size() != other.vv1.size()) {
+            return false;
+        }
+        // need to check if they are both nan
+        for(std::size_t index = 0; index < vv1.size(); ++index) {
+            if(vv1[index] != other.vv1[index]) {
+                if(std::isnan(vv1[index]) && std::isnan(other.vv1[index])) {
+                    continue;
+                }
+                return false;
+            }
+        }
     }
     if(vstr != other.vstr) {
         return false;
diff --git a/include/CLI/impl/App_inl.hpp b/include/CLI/impl/App_inl.hpp
index 10e0a568..2e17cb89 100644
--- a/include/CLI/impl/App_inl.hpp
+++ b/include/CLI/impl/App_inl.hpp
@@ -1951,7 +1951,7 @@ App::_parse_arg(std::vector<std::string> &args, detail::Classifier current_type,
 
         // now check for '.' notation of subcommands
         auto dotloc = arg_name.find_first_of('.', 1);
-        if(dotloc != std::string::npos) {
+        if(dotloc != std::string::npos && dotloc < arg_name.size() - 1) {
             // using dot notation is equivalent to single argument subcommand
             auto *sub = _find_subcommand(arg_name.substr(0, dotloc), true, false);
             if(sub != nullptr) {
@@ -1972,7 +1972,12 @@ App::_parse_arg(std::vector<std::string> &args, detail::Classifier current_type,
                     args.push_back(nval);
                     current_type = detail::Classifier::SHORT;
                 }
-                auto val = sub->_parse_arg(args, current_type, true);
+                std::string dummy1, dummy2;
+                bool val = false;
+                if(current_type == detail::Classifier::SHORT || detail::split_long(args.back(), dummy1, dummy2)) {
+                    val = sub->_parse_arg(args, current_type, true);
+                }
+
                 if(val) {
                     if(!sub->silent_) {
                         parsed_subcommands_.push_back(sub);
diff --git a/tests/FuzzFailTest.cpp b/tests/FuzzFailTest.cpp
index 45617f50..683214a9 100644
--- a/tests/FuzzFailTest.cpp
+++ b/tests/FuzzFailTest.cpp
@@ -306,14 +306,13 @@ TEST_CASE("fuzz_config_modifier_test1") {
     CHECK(opt3->get_multi_option_policy() == CLI::MultiOptionPolicy::Sum);
 }
 
-// this test uses the same tests as above just with a full roundtrip test
+// this test enables the custom option creation operation
 TEST_CASE("app_roundtrip_custom") {
     CLI::FuzzApp fuzzdata;
     CLI::FuzzApp fuzzdata2;
     auto app = fuzzdata.generateApp();
     auto app2 = fuzzdata2.generateApp();
-    int index = GENERATE(range(1, 4));
-    std::string optionString, flagString;
+    int index = GENERATE(range(1, 5));
     auto parseData = loadFailureFile("round_trip_custom", index);
     std::size_t pstring_start{0};
     pstring_start = fuzzdata.add_custom_options(app.get(), parseData);
@@ -335,3 +334,43 @@ TEST_CASE("app_roundtrip_custom") {
     auto result = fuzzdata2.compare(fuzzdata);
     CHECK(result);
 }
+
+// this test
+TEST_CASE("app_roundtrip_parse_normal_fail") {
+    // this is mostly checking that no unexpected errors occur
+    // like HorribleErrors
+    CLI::FuzzApp fuzzdata;
+    auto app = fuzzdata.generateApp();
+    int index = GENERATE(range(1, 3));
+    std::string optionString, flagString;
+    auto parseData = loadFailureFile("parse_fail_check", index);
+    std::size_t pstring_start{0};
+    pstring_start = fuzzdata.add_custom_options(app.get(), parseData);
+
+    try {
+        if(pstring_start > 0) {
+            app->parse(parseData.substr(pstring_start));
+        } else {
+            app->parse(parseData);
+        }
+    } catch(const CLI::HorribleError & /*he*/) {
+        CHECK(false);
+        return;
+    } catch(const CLI::ParseError & /*e*/) {
+        CHECK(true);
+        return;
+    }
+    try {
+        // should be able to write the config to a file and read from it again
+        std::string configOut = app->config_to_str();
+        app->clear();
+        std::stringstream out(configOut);
+        app->parse_from_stream(out);
+    } catch(const CLI::HorribleError & /*he*/) {
+        CHECK(false);
+        return;
+    } catch(const CLI::ParseError & /*e*/) {
+        CHECK(false);
+        return;
+    }
+}
diff --git a/tests/fuzzFail/parse_fail_check1 b/tests/fuzzFail/parse_fail_check1
new file mode 100644
index 00000000..1d5d319b
--- /dev/null
+++ b/tests/fuzzFail/parse_fail_check1
@@ -0,0 +1 @@
+'--sub1.!-vA '
\ No newline at end of file
diff --git a/tests/fuzzFail/parse_fail_check2 b/tests/fuzzFail/parse_fail_check2
new file mode 100644
index 00000000..a6ca3994
Binary files /dev/null and b/tests/fuzzFail/parse_fail_check2 differ
diff --git a/tests/fuzzFail/round_trip_custom4 b/tests/fuzzFail/round_trip_custom4
new file mode 100644
index 00000000..b8202d71
--- /dev/null
+++ b/tests/fuzzFail/round_trip_custom4
@@ -0,0 +1 @@
+--vC
=-vA --vopt1=
nan
\ No newline at end of file