diff --git a/src/commands/classified.rs b/src/commands/classified.rs
index 45262bfee..309af2441 100644
--- a/src/commands/classified.rs
+++ b/src/commands/classified.rs
@@ -140,19 +140,21 @@ impl InternalCommand {
                     }
                     CommandAction::Exit => std::process::exit(0),
                     CommandAction::EnterValueShell(value) => {
-                        context.shell_manager.push(Box::new(ValueShell::new(value)));
+                        context
+                            .shell_manager
+                            .insert_at_current(Box::new(ValueShell::new(value)));
                     }
                     CommandAction::EnterShell(location) => {
                         let path = std::path::Path::new(&location);
 
                         if path.is_dir() {
                             // If it's a directory, add a new filesystem shell
-                            context
-                                .shell_manager
-                                .push(Box::new(FilesystemShell::with_location(
+                            context.shell_manager.insert_at_current(Box::new(
+                                FilesystemShell::with_location(
                                     location,
                                     context.registry().clone(),
-                                )?));
+                                )?,
+                            ));
                         } else {
                             // If it's a file, attempt to open the file as a value and enter it
                             let cwd = context.shell_manager.path();
@@ -180,11 +182,13 @@ impl InternalCommand {
                                         Span::unknown(),
                                     )?;
 
-                                    context.shell_manager.push(Box::new(ValueShell::new(value)));
+                                    context
+                                        .shell_manager
+                                        .insert_at_current(Box::new(ValueShell::new(value)));
                                 }
-                                value => context
-                                    .shell_manager
-                                    .push(Box::new(ValueShell::new(value.tagged(contents_tag)))),
+                                value => context.shell_manager.insert_at_current(Box::new(
+                                    ValueShell::new(value.tagged(contents_tag)),
+                                )),
                             }
                         }
                     }
@@ -195,7 +199,7 @@ impl InternalCommand {
                         context.shell_manager.next();
                     }
                     CommandAction::LeaveShell => {
-                        context.shell_manager.pop();
+                        context.shell_manager.remove_at_current();
                         if context.shell_manager.is_empty() {
                             std::process::exit(0);
                         }
diff --git a/src/commands/shells.rs b/src/commands/shells.rs
index 9aa65bdfc..f31a16fd5 100644
--- a/src/commands/shells.rs
+++ b/src/commands/shells.rs
@@ -27,12 +27,10 @@ fn shells(args: CommandArgs, _registry: &CommandRegistry) -> Result<OutputStream
     let mut shells_out = VecDeque::new();
     let span = args.call_info.name_span;
 
-    let shells_len = args.shell_manager.shells.lock().unwrap().len();
-
     for (index, shell) in args.shell_manager.shells.lock().unwrap().iter().enumerate() {
         let mut dict = TaggedDictBuilder::new(Tag::unknown_origin(span));
 
-        if index == (shells_len - 1) {
+        if index == args.shell_manager.current_shell {
             dict.insert(" ", "X".to_string());
         } else {
             dict.insert(" ", " ".to_string());
diff --git a/src/object/base.rs b/src/object/base.rs
index 9ad81b451..ea86386c6 100644
--- a/src/object/base.rs
+++ b/src/object/base.rs
@@ -354,7 +354,16 @@ impl Value {
 
         if let Value::Object(ref mut o) = new_obj {
             let mut current = o;
-            for idx in 0..split_path.len() - 1 {
+
+            if split_path.len() == 1 {
+                // Special case for inserting at the top level
+                current
+                    .entries
+                    .insert(path.to_string(), Tagged::from_item(new_value, tag));
+                return Some(Tagged::from_item(new_obj, tag));
+            }
+
+            for idx in 0..split_path.len() {
                 match current.entries.get_mut(split_path[idx]) {
                     Some(next) => {
                         if idx == (split_path.len() - 2) {
diff --git a/src/parser/deserializer.rs b/src/parser/deserializer.rs
index fe0289aa0..b2cc00ac6 100644
--- a/src/parser/deserializer.rs
+++ b/src/parser/deserializer.rs
@@ -1,5 +1,3 @@
-use crate::commands::command::EvaluatedCommandArgs;
-use crate::parser::registry::EvaluatedArgs;
 use crate::prelude::*;
 use log::trace;
 use serde::{de, forward_to_deserialize_any};
diff --git a/src/plugins/add.rs b/src/plugins/add.rs
index 11b90de63..2634c1497 100644
--- a/src/plugins/add.rs
+++ b/src/plugins/add.rs
@@ -23,9 +23,10 @@ impl Add {
                 Some(f) => match obj.insert_data_at_path(value_tag, &f, v) {
                     Some(v) => return Ok(v),
                     None => {
-                        return Err(ShellError::string(
-                            "add could not find place to insert field",
-                        ))
+                        return Err(ShellError::string(format!(
+                            "add could not find place to insert field {:?} {}",
+                            obj, f
+                        )))
                     }
                 },
                 None => Err(ShellError::string(
diff --git a/src/prelude.rs b/src/prelude.rs
index eec943a99..9e1f7322f 100644
--- a/src/prelude.rs
+++ b/src/prelude.rs
@@ -41,7 +41,7 @@ crate use crate::context::CommandRegistry;
 crate use crate::context::{Context, SpanSource};
 crate use crate::env::host::handle_unexpected;
 crate use crate::env::Host;
-crate use crate::errors::{ShellError, ShellErrorUtils};
+crate use crate::errors::ShellError;
 crate use crate::object::base as value;
 crate use crate::object::meta::{Tag, Tagged, TaggedItem};
 crate use crate::object::types::ExtractType;
diff --git a/src/shell/shell_manager.rs b/src/shell/shell_manager.rs
index bce931c51..d8f63ceb0 100644
--- a/src/shell/shell_manager.rs
+++ b/src/shell/shell_manager.rs
@@ -9,25 +9,44 @@ use std::sync::{Arc, Mutex};
 
 #[derive(Clone, Debug)]
 pub struct ShellManager {
+    crate current_shell: usize,
     crate shells: Arc<Mutex<Vec<Box<dyn Shell + Send>>>>,
 }
 
 impl ShellManager {
     pub fn basic(commands: CommandRegistry) -> Result<ShellManager, Box<dyn Error>> {
         Ok(ShellManager {
+            current_shell: 0,
             shells: Arc::new(Mutex::new(vec![Box::new(FilesystemShell::basic(
                 commands,
             )?)])),
         })
     }
 
-    pub fn push(&mut self, shell: Box<dyn Shell + Send>) {
+    pub fn insert_at_current(&mut self, shell: Box<dyn Shell + Send>) {
         self.shells.lock().unwrap().push(shell);
+        self.current_shell = self.shells.lock().unwrap().len() - 1;
         self.set_path(self.path());
     }
 
-    pub fn pop(&mut self) {
-        self.shells.lock().unwrap().pop();
+    pub fn remove_at_current(&mut self) {
+        {
+            let mut shells = self.shells.lock().unwrap();
+            if shells.len() > 0 {
+                if self.current_shell == shells.len() - 1 {
+                    shells.pop();
+                    let new_len = shells.len();
+                    if new_len > 0 {
+                        self.current_shell = new_len - 1;
+                    } else {
+                        return;
+                    }
+                } else {
+                    shells.remove(self.current_shell);
+                }
+            }
+        }
+        self.set_path(self.path());
     }
 
     pub fn is_empty(&self) -> bool {
@@ -35,16 +54,11 @@ impl ShellManager {
     }
 
     pub fn path(&self) -> String {
-        self.shells.lock().unwrap().last().unwrap().path()
+        self.shells.lock().unwrap()[self.current_shell].path()
     }
 
     pub fn set_path(&mut self, path: String) {
-        self.shells
-            .lock()
-            .unwrap()
-            .last_mut()
-            .unwrap()
-            .set_path(path)
+        self.shells.lock().unwrap()[self.current_shell].set_path(path)
     }
 
     pub fn complete(
@@ -53,37 +67,33 @@ impl ShellManager {
         pos: usize,
         ctx: &rustyline::Context<'_>,
     ) -> Result<(usize, Vec<rustyline::completion::Pair>), rustyline::error::ReadlineError> {
-        self.shells
-            .lock()
-            .unwrap()
-            .last()
-            .unwrap()
-            .complete(line, pos, ctx)
+        self.shells.lock().unwrap()[self.current_shell].complete(line, pos, ctx)
     }
 
     pub fn hint(&self, line: &str, pos: usize, ctx: &rustyline::Context<'_>) -> Option<String> {
-        self.shells
-            .lock()
-            .unwrap()
-            .last()
-            .unwrap()
-            .hint(line, pos, ctx)
+        self.shells.lock().unwrap()[self.current_shell].hint(line, pos, ctx)
     }
 
     pub fn next(&mut self) {
         {
-            let mut x = self.shells.lock().unwrap();
-            let shell = x.remove(0);
-            x.push(shell);
+            let shell_len = self.shells.lock().unwrap().len();
+            if self.current_shell == (shell_len - 1) {
+                self.current_shell = 0;
+            } else {
+                self.current_shell += 1;
+            }
         }
         self.set_path(self.path());
     }
 
     pub fn prev(&mut self) {
         {
-            let mut x = self.shells.lock().unwrap();
-            let shell = x.pop().unwrap();
-            x.insert(0, shell);
+            let shell_len = self.shells.lock().unwrap().len();
+            if self.current_shell == 0 {
+                self.current_shell = shell_len - 1;
+            } else {
+                self.current_shell -= 1;
+            }
         }
         self.set_path(self.path());
     }
@@ -91,11 +101,11 @@ impl ShellManager {
     pub fn ls(&self, args: EvaluatedWholeStreamCommandArgs) -> Result<OutputStream, ShellError> {
         let env = self.shells.lock().unwrap();
 
-        env.last().unwrap().ls(args)
+        env[self.current_shell].ls(args)
     }
     pub fn cd(&self, args: EvaluatedWholeStreamCommandArgs) -> Result<OutputStream, ShellError> {
         let env = self.shells.lock().unwrap();
 
-        env.last().unwrap().cd(args)
+        env[self.current_shell].cd(args)
     }
 }
diff --git a/tests/command_enter_test.rs b/tests/command_enter_test.rs
index 051d19467..077c1f66c 100644
--- a/tests/command_enter_test.rs
+++ b/tests/command_enter_test.rs
@@ -48,6 +48,7 @@ fn knows_the_filesystems_entered() {
             cd ..
             rm red_pill --recursive
             exit
+            n
             rm blue_pill --recursive
             exit
         "#