diff --git a/CHANGELOG.md b/CHANGELOG.md
index 689794ad..803dfd18 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -2,6 +2,9 @@
 
 ## Unreleased
 
+- Fixed a bug where an environment in a Taskfile was not always overridable
+  by the system environment
+  ([#425](https://github.com/go-task/task/issues/425)).
 - Fixed environment from .env files not being available as variables
   ([#379](https://github.com/go-task/task/issues/379)).
 
diff --git a/task.go b/task.go
index 92432306..fbefd531 100644
--- a/task.go
+++ b/task.go
@@ -397,10 +397,19 @@ func getEnviron(t *taskfile.Task) []string {
 	}
 
 	environ := os.Environ()
+
 	for k, v := range t.Env.ToCacheMap() {
-		if s, ok := v.(string); ok {
-			environ = append(environ, fmt.Sprintf("%s=%s", k, s))
+		str, isString := v.(string)
+		if !isString {
+			continue
 		}
+
+		if _, alreadySet := os.LookupEnv(k); alreadySet {
+			continue
+		}
+
+		environ = append(environ, fmt.Sprintf("%s=%s", k, str))
 	}
+
 	return environ
 }