diff --git a/src/commands/from_json.rs b/src/commands/from_json.rs
index f64fc031a7..3a984bac6d 100644
--- a/src/commands/from_json.rs
+++ b/src/commands/from_json.rs
@@ -18,13 +18,17 @@ fn convert_json_value_to_nu_value(v: &serde_json::Value) -> Value {
     }
 }
 
+pub fn from_json_string_to_value(s: String) -> Value {
+    let v: serde_json::Value = serde_json::from_str(&s).unwrap();
+    convert_json_value_to_nu_value(&v)
+}
+
 pub fn from_json(args: CommandArgs) -> Result<OutputStream, ShellError> {
     let out = args.input;
     Ok(out
         .map(|a| match a {
             Value::Primitive(Primitive::String(s)) => {
-                let v: serde_json::Value = serde_json::from_str(&s).unwrap();
-                ReturnValue::Value(convert_json_value_to_nu_value(&v))
+                ReturnValue::Value(from_json_string_to_value(s))
             }
             _ => ReturnValue::Value(Value::Primitive(Primitive::String("".to_string()))),
         })
diff --git a/src/commands/from_toml.rs b/src/commands/from_toml.rs
index 38c87409fa..59610a8ffd 100644
--- a/src/commands/from_toml.rs
+++ b/src/commands/from_toml.rs
@@ -20,13 +20,17 @@ fn convert_toml_value_to_nu_value(v: &toml::Value) -> Value {
     }
 }
 
+pub fn from_toml_string_to_value(s: String) -> Value {
+    let v: toml::Value = s.parse::<toml::Value>().unwrap();
+    convert_toml_value_to_nu_value(&v)
+}
+
 pub fn from_toml(args: CommandArgs) -> Result<OutputStream, ShellError> {
     let out = args.input;
     Ok(out
         .map(|a| match a {
             Value::Primitive(Primitive::String(s)) => {
-                let v: toml::Value = s.parse::<toml::Value>().unwrap();
-                ReturnValue::Value(convert_toml_value_to_nu_value(&v))
+                ReturnValue::Value(from_toml_string_to_value(s))
             }
             _ => ReturnValue::Value(Value::Primitive(Primitive::String("".to_string()))),
         })
diff --git a/src/commands/open.rs b/src/commands/open.rs
index cce5b76649..4e9a17b2ee 100644
--- a/src/commands/open.rs
+++ b/src/commands/open.rs
@@ -14,9 +14,25 @@ pub fn open(args: CommandArgs) -> Result<OutputStream, ShellError> {
     let contents = std::fs::read_to_string(&full_path).unwrap();
 
     let mut stream = VecDeque::new();
-    stream.push_back(ReturnValue::Value(Value::Primitive(Primitive::String(
-        contents,
-    ))));
+
+    let open_raw = match args.positional.get(1) {
+        Some(Value::Primitive(Primitive::String(s))) if s == "--raw" => true,
+        _ => false,
+    };
+
+    match full_path.extension() {
+        Some(x) if x == "toml" && !open_raw => {
+            stream.push_back(ReturnValue::Value(crate::commands::from_toml::from_toml_string_to_value(contents)));
+        }
+        Some(x) if x == "json" && !open_raw => {
+            stream.push_back(ReturnValue::Value(crate::commands::from_json::from_json_string_to_value(contents)));
+        }
+        _ => {
+            stream.push_back(ReturnValue::Value(Value::Primitive(Primitive::String(
+                contents,
+            ))));
+        }
+    }
 
     Ok(stream.boxed())
 }
diff --git a/src/evaluate/evaluator.rs b/src/evaluate/evaluator.rs
index 71eab8b134..0ce95a7338 100644
--- a/src/evaluate/evaluator.rs
+++ b/src/evaluate/evaluator.rs
@@ -1,5 +1,6 @@
 use crate::parser::ast;
 use crate::prelude::*;
+use crate::object::Primitive;
 use derive_new::new;
 
 #[derive(new)]
@@ -20,10 +21,7 @@ crate fn evaluate_expr(expr: &ast::Expression, scope: &Scope) -> Result<Value, S
     match expr {
         Expression::Leaf(l) => Ok(evaluate_leaf(l)),
         Expression::Parenthesized(p) => evaluate_expr(&p.expr, scope),
-        Expression::Flag(f) => Err(ShellError::string(format!(
-            "can't evaluate the flag {}",
-            f.print()
-        ))),
+        Expression::Flag(f) => Ok(Value::Primitive(Primitive::String(f.print()))),
         Expression::Block(b) => evaluate_block(&b, scope),
         Expression::Path(p) => evaluate_path(&p, scope),
         Expression::Binary(b) => evaluate_binary(b, scope),