diff --git a/crates/nu-cli/src/commands/autoenv.rs b/crates/nu-cli/src/commands/autoenv.rs
index 57800c311f..bc91506ed4 100644
--- a/crates/nu-cli/src/commands/autoenv.rs
+++ b/crates/nu-cli/src/commands/autoenv.rs
@@ -4,9 +4,9 @@ use nu_errors::ShellError;
 use nu_protocol::{ReturnSuccess, Signature, UntaggedValue};
 use serde::Deserialize;
 use serde::Serialize;
-use sha2::{Digest, Sha256};
 use std::io::Read;
 use std::path::PathBuf;
+
 pub struct Autoenv;
 
 #[derive(Deserialize, Serialize, Debug, Default)]
@@ -19,54 +19,26 @@ impl Trusted {
             files: IndexMap::new(),
         }
     }
+    pub fn read_trusted() -> Result<Self, ShellError> {
+        let config_path = config::default_path_for(&Some(PathBuf::from("nu-env.toml")))?;
 
-    pub fn read_trusted() -> Result<Trusted, ShellError> {
-        let allowed = Trusted {
-            files: read_config_file()?,
-        };
+        let mut file = std::fs::OpenOptions::new()
+            .read(true)
+            .create(true)
+            .write(true)
+            .open(config_path)
+            .or_else(|_| {
+                Err(ShellError::untagged_runtime_error(
+                    "Couldn't open nu-env.toml",
+                ))
+            })?;
+        let mut doc = String::new();
+        file.read_to_string(&mut doc)?;
+
+        let allowed: Trusted = toml::from_str(doc.as_str()).unwrap_or_else(|_| Trusted::new());
         Ok(allowed)
     }
-    pub fn file_is_trusted_reload_config(
-        &mut self,
-        nu_env_file: &PathBuf,
-        content: &Vec<u8>,
-    ) -> Result<bool, ShellError> {
-        let contentdigest = Sha256::digest(&content).as_slice().to_vec();
-        let nufile = nu_env_file.to_str().unwrap_or("");
-
-        //If the existing hash for nu_env_file exists and corresponds to the hash of content, everything is fine.
-        if self.files.get(nufile) == Some(&contentdigest) {
-            return Ok(true);
-        }
-        //Otherwise, we re-read the hash from nu-env.toml and compare with that. If it is the same, we update the map.
-        //This allows the user to use autoenv trust without having to restart nushell afterwards
-        // let current_config = read_config_file()?;
-        // if current_config.get(nufile) == Some(&contentdigest) {
-        //     self.files = current_config;
-        //     return Ok(true);
-        // }
-        Ok(false)
-    }
 }
-
-fn read_config_file() -> Result<IndexMap<String, Vec<u8>>, ShellError> {
-    let config_path = config::default_path_for(&Some(PathBuf::from("nu-env.toml")))?;
-
-    let mut file = std::fs::OpenOptions::new()
-        .read(true)
-        .create(true)
-        .write(true)
-        .open(config_path)
-        .or_else(|_| {
-            Err(ShellError::untagged_runtime_error(
-                "Couldn't open nu-env.toml",
-            ))
-        })?;
-    let mut doc = String::new();
-    file.read_to_string(&mut doc)?;
-    Ok(toml::from_str(doc.as_str()).unwrap_or_else(|_| IndexMap::new()))
-}
-
 #[async_trait]
 impl WholeStreamCommand for Autoenv {
     fn name(&self) -> &str {
diff --git a/crates/nu-cli/src/env/directory_specific_environment.rs b/crates/nu-cli/src/env/directory_specific_environment.rs
index 7d32c5bc1d..23d59f0fac 100644
--- a/crates/nu-cli/src/env/directory_specific_environment.rs
+++ b/crates/nu-cli/src/env/directory_specific_environment.rs
@@ -36,11 +36,12 @@ impl DirectorySpecificEnvironment {
         }
     }
 
-    fn toml_if_directory_is_trusted(&mut self, nu_env_file: &PathBuf) -> Result<toml::Value, ShellError> {
-        if let Some(trusted) = self.trusted.as_mut() {
+    fn toml_if_directory_is_trusted(&self, nu_env_file: &PathBuf) -> Result<toml::Value, ShellError> {
+        if let Some(trusted) = &self.trusted {
             let content = std::fs::read(&nu_env_file)?;
 
-            if trusted.file_is_trusted_reload_config(&nu_env_file, &content)?
+            if trusted.files.get(nu_env_file.to_str().unwrap_or(""))
+                == Some(&Sha256::digest(&content).as_slice().to_vec())
             {
                 return Ok(std::str::from_utf8(&content.as_slice()).or_else(|_| {
                     Err(ShellError::untagged_runtime_error(format!("Could not read {:?} as utf8 string", content)))
@@ -65,6 +66,8 @@ impl DirectorySpecificEnvironment {
 
         //If we are in the last seen directory, do nothing
         //If we are in a parent directory to last_seen_directory, just return without applying .nu-env in the parent directory - they were already applied earlier.
+        //If current dir is parent to last_seen_directory, current.cmp(last) returns less
+        //if current dir is the same as last_seen, current.cmp(last) returns equal
         while self.last_seen_directory.cmp(&working_dir) == std::cmp::Ordering::Less { //parent.cmp(child) = Less
             if nu_env_file.exists() {
                 let toml_doc = self.toml_if_directory_is_trusted(&nu_env_file)?;