diff --git a/cmd/cmd_update.go b/cmd/cmd_update.go
index 9e97d1d..ae0ff2d 100644
--- a/cmd/cmd_update.go
+++ b/cmd/cmd_update.go
@@ -51,7 +51,7 @@ var updateCommand = &cli.Command{
 
 		// Copy source to "new"
 		fmt.Print("Copying .env.source into .env.merged")
-		if err := Copy(".env.merged", ".env.source"); err != nil {
+		if err := Copy(".env.source", ".env.merged"); err != nil {
 			return err
 		}
 		fmt.Println(" ✅")
@@ -67,17 +67,19 @@ var updateCommand = &cli.Command{
 		// Take current assignments and set them in the new doc
 		fmt.Println("Updating .env.merged with key/value pairs from .env")
 		for _, stmt := range env.Assignments() {
-			if stmt.Active {
+			if !stmt.Active {
 				continue
 			}
 
-			changed, err := mergedEnv.Set(&ast.Assignment{Name: stmt.Name, Literal: stmt.Literal}, ast.SetOptions{SkipIfSame: true})
+			changed, err := mergedEnv.Set(stmt, ast.SetOptions{SkipIfSame: true, ErrorIfMissing: true})
 			if err != nil {
-				return err
+				fmt.Println("  ❌", err.Error())
+
+				continue
 			}
 
 			if changed {
-				fmt.Println("  ✅", stmt.Name)
+				fmt.Println("  ✅", fmt.Sprintf("Key [%s] was successfully updated", stmt.Name))
 			}
 		}
 
@@ -88,7 +90,7 @@ var updateCommand = &cli.Command{
 	},
 }
 
-func Copy(dst, src string) error {
+func Copy(src, dst string) error {
 	srcF, err := os.Open(src)
 	if err != nil {
 		return err
diff --git a/pkg/ast/document.go b/pkg/ast/document.go
index 081bc0f..0e4b247 100644
--- a/pkg/ast/document.go
+++ b/pkg/ast/document.go
@@ -38,23 +38,23 @@ func (d *Document) statementNode() {
 }
 
 func (d *Document) Assignments() []*Assignment {
-	var values []*Assignment
+	var assignments []*Assignment
 
-	for _, stmt := range d.Statements {
-		if assign, ok := stmt.(*Assignment); ok {
-			values = append(values, assign)
+	for _, statement := range d.Statements {
+		if assign, ok := statement.(*Assignment); ok {
+			assignments = append(assignments, assign)
 		}
 	}
 
-	for _, grp := range d.Groups {
-		for _, stmt := range grp.Statements {
-			if assign, ok := stmt.(*Assignment); ok {
-				values = append(values, assign)
+	for _, group := range d.Groups {
+		for _, statement := range group.Statements {
+			if assignment, ok := statement.(*Assignment); ok {
+				assignments = append(assignments, assignment)
 			}
 		}
 	}
 
-	return values
+	return assignments
 }
 
 func (d *Document) GetGroup(name string) *Group {