diff --git a/AK/Error.h b/AK/Error.h
index 1346cb02d9..b25e8348ee 100644
--- a/AK/Error.h
+++ b/AK/Error.h
@@ -21,9 +21,11 @@ namespace AK {
 class Error {
 public:
     static Error from_errno(int code) { return Error(code); }
+    static Error from_syscall(StringView syscall_name, int rc) { return Error(syscall_name, rc); }
     static Error from_string_literal(StringView string_literal) { return Error(string_literal); }
 
     bool is_errno() const { return m_code != 0; }
+    bool is_syscall() const { return m_syscall; }
 
     int code() const { return m_code; }
     StringView string_literal() const { return m_string_literal; }
@@ -40,8 +42,16 @@ private:
     {
     }
 
+    Error(StringView syscall_name, int rc)
+        : m_code(-rc)
+        , m_string_literal(syscall_name)
+        , m_syscall(true)
+    {
+    }
+
     int m_code { 0 };
     StringView m_string_literal;
+    bool m_syscall { false };
 };
 
 template<typename T, typename ErrorType>
diff --git a/Userland/Libraries/LibMain/Main.cpp b/Userland/Libraries/LibMain/Main.cpp
index 1cee6c2e49..6c1c76425a 100644
--- a/Userland/Libraries/LibMain/Main.cpp
+++ b/Userland/Libraries/LibMain/Main.cpp
@@ -8,6 +8,7 @@
 #include <AK/StringView.h>
 #include <AK/Vector.h>
 #include <LibMain/Main.h>
+#include <string.h>
 
 int main(int argc, char** argv)
 {
@@ -22,7 +23,13 @@ int main(int argc, char** argv)
         .arguments = arguments.span(),
     });
     if (result.is_error()) {
-        warnln("Runtime error: {}", result.error());
+        auto error = result.release_error();
+        if (error.is_syscall())
+            warnln("Runtime error: {}: {} (errno={})", error.string_literal(), strerror(error.code()), error.code());
+        else if (error.is_errno())
+            warnln("Runtime error: {} (errno={})", strerror(error.code()), error.code());
+        else
+            warnln("Runtime error: {}", error.string_literal());
         return 1;
     }
     return result.value();
diff --git a/Userland/Libraries/LibSystem/Wrappers.cpp b/Userland/Libraries/LibSystem/Wrappers.cpp
index 7045d7c786..a614c732e6 100644
--- a/Userland/Libraries/LibSystem/Wrappers.cpp
+++ b/Userland/Libraries/LibSystem/Wrappers.cpp
@@ -7,6 +7,12 @@
 #include <LibSystem/Wrappers.h>
 #include <LibSystem/syscall.h>
 
+#define HANDLE_SYSCALL_RETURN_VALUE(syscall_name, rc) \
+    if ((rc) < 0) {                                   \
+        return Error::from_syscall(syscall_name, rc); \
+    }                                                 \
+    return {};
+
 namespace System {
 
 ErrorOr<void> pledge(StringView promises, StringView execpromises)
@@ -16,9 +22,7 @@ ErrorOr<void> pledge(StringView promises, StringView execpromises)
         { execpromises.characters_without_null_termination(), execpromises.length() },
     };
     int rc = syscall(SC_pledge, &params);
-    if (rc < 0)
-        return Error::from_errno(-rc);
-    return {};
+    HANDLE_SYSCALL_RETURN_VALUE("pledge"sv, rc);
 }
 
 ErrorOr<void> unveil(StringView path, StringView permissions)
@@ -28,9 +32,7 @@ ErrorOr<void> unveil(StringView path, StringView permissions)
         { permissions.characters_without_null_termination(), permissions.length() },
     };
     int rc = syscall(SC_unveil, &params);
-    if (rc < 0)
-        return Error::from_errno(-rc);
-    return {};
+    HANDLE_SYSCALL_RETURN_VALUE("unveil"sv, rc);
 }
 
 }