diff --git a/src/build_settings.cpp b/src/build_settings.cpp
index c12107bf7..006b0ea0a 100644
--- a/src/build_settings.cpp
+++ b/src/build_settings.cpp
@@ -2215,18 +2215,18 @@ gb_internal bool check_target_feature_is_enabled(String const &feature, String *
 		}
 		if (feature_str == "") break;
 
-		if (!string_set_exists(&build_context.target_features_set, str)) {
-			String plus_str = concatenate_strings(temporary_allocator(), make_string_c("+"), feature_str);
-
-			if (want_enabled && !string_set_exists(&build_context.target_features_set, plus_str)) {
-				if (not_enabled) *not_enabled = str;
-				return false;
-			}
-		}
-
+		String plus_str  = concatenate_strings(temporary_allocator(), make_string_c("+"), feature_str);
 		String minus_str = concatenate_strings(temporary_allocator(), make_string_c("-"), feature_str);
-
-		if (!want_enabled && !string_set_exists(&build_context.target_features_set, minus_str)) {
+		
+		bool has_raw   = string_set_exists(&build_context.target_features_set, feature_str);
+		bool has_plus  = string_set_exists(&build_context.target_features_set, plus_str);
+		bool has_minus = string_set_exists(&build_context.target_features_set, minus_str);
+		
+		// NOTE(jakubtomsu): this way "feature" and "+feature" is ALWAYS equivalent,
+		// and also allows the minus sign to do a final override.
+		bool is_enabled = (has_plus || has_raw) && !has_minus;
+		
+		if (want_enabled != is_enabled) {
 			if (not_enabled) *not_enabled = str;
 			return false;
 		}
diff --git a/src/main.cpp b/src/main.cpp
index 18381f5ee..b4ad8168b 100644
--- a/src/main.cpp
+++ b/src/main.cpp
@@ -3973,15 +3973,16 @@ int main(int arg_count, char const **arg_ptr) {
 		for (;;) {
 			String item = string_split_iterator(&target_it, ',');
 			if (item == "") break;
-
-			if (*item.text == '+' || *item.text == '-') {
-				item.text++;
-				item.len--;
+			
+			String stripped_item = item;
+			if (*stripped_item.text == '+' || *stripped_item.text == '-') {
+				stripped_item.text++;
+				stripped_item.len--;
 			}
 
 			String invalid;
-			if (!check_target_feature_is_valid_for_target_arch(item, &invalid) && item != str_lit("help")) {
-				if (item != str_lit("?")) {
+			if (!check_target_feature_is_valid_for_target_arch(stripped_item, &invalid) && stripped_item != str_lit("help")) {
+				if (stripped_item != str_lit("?")) {
 					gb_printf_err("Unkown target feature '%.*s'.\n", LIT(invalid));
 				}
 				gb_printf("Possible -target-features for target %.*s are:\n", LIT(target_arch_names[build_context.metrics.arch]));
@@ -4005,8 +4006,25 @@ int main(int arg_count, char const **arg_ptr) {
 
 				return 1;
 			}
-
-			string_set_add(&build_context.target_features_set, item);
+			
+			// Ensure the feature name always has +/- prefix. If there isn't, default to '+'
+			String feature_str = item;
+			if (*feature_str.text != '+' && *feature_str.text != '-') {
+				feature_str = concatenate_strings(temporary_allocator(), make_string_c("+"), feature_str);
+			}
+			
+			// Ensure there is only a single entry for each feature in the target set.
+			// If the negative exists, override the existing value with the current one.
+			String neg_feature_str = clone_string(temporary_allocator(), feature_str);
+			switch (*neg_feature_str.text) {
+				case '+': *neg_feature_str.text = '-'; break;
+				case '-': *neg_feature_str.text = '+'; break;
+				default: GB_ASSERT(false); break;
+			}
+			
+			string_set_remove(&build_context.target_features_set, neg_feature_str);
+			
+			string_set_add(&build_context.target_features_set, feature_str);
 		}
 	}
 
diff --git a/src/string.cpp b/src/string.cpp
index a4fa85871..977327bcd 100644
--- a/src/string.cpp
+++ b/src/string.cpp
@@ -508,6 +508,13 @@ gb_internal String filename_without_directory(String s) {
 	return substring(s, gb_max(j+1, 0), s.len);
 }
 
+gb_internal String clone_string(gbAllocator a, String const &x) {
+	u8 *data = gb_alloc_array(a, u8, x.len+1);
+	gb_memmove(data, x.text, x.len);
+	data[x.len] = 0;
+	return make_string(data, x.len);
+}
+
 gb_internal String concatenate_strings(gbAllocator a, String const &x, String const &y) {
 	isize len = x.len+y.len;
 	u8 *data = gb_alloc_array(a, u8, len+1);