diff --git a/crates/nu-cli/src/repl.rs b/crates/nu-cli/src/repl.rs
index 1fe5109cfc..47b89f8bd8 100644
--- a/crates/nu-cli/src/repl.rs
+++ b/crates/nu-cli/src/repl.rs
@@ -19,7 +19,7 @@ use miette::{ErrReport, IntoDiagnostic, Result};
 use nu_cmd_base::util::get_editor;
 use nu_color_config::StyleComputer;
 #[allow(deprecated)]
-use nu_engine::{current_dir_str, env_to_strings};
+use nu_engine::{convert_env_values, current_dir_str, env_to_strings};
 use nu_parser::{lex, parse, trim_quotes_str};
 use nu_protocol::{
     config::NuCursorShape,
@@ -79,6 +79,13 @@ pub fn evaluate_repl(
         stack.clone(),
     );
 
+    let start_time = std::time::Instant::now();
+    // Translate environment variables from Strings to Values
+    if let Err(e) = convert_env_values(engine_state, &unique_stack) {
+        report_shell_error(engine_state, &e);
+    }
+    perf!("translate env vars", start_time, use_color);
+
     // seed env vars
     unique_stack.add_env_var(
         "CMD_DURATION_MS".into(),
diff --git a/crates/nu-engine/src/env.rs b/crates/nu-engine/src/env.rs
index 0d3fde7de6..54f800958f 100644
--- a/crates/nu-engine/src/env.rs
+++ b/crates/nu-engine/src/env.rs
@@ -89,7 +89,22 @@ pub fn convert_env_values(engine_state: &mut EngineState, stack: &Stack) -> Resu
         }
     }
 
-    error = error.or_else(|| ensure_path(&mut new_scope, "PATH"));
+    #[cfg(not(windows))]
+    {
+        error = error.or_else(|| ensure_path(&mut new_scope, "PATH"));
+    }
+
+    #[cfg(windows)]
+    {
+        let first_result = ensure_path(&mut new_scope, "Path");
+        if first_result.is_some() {
+            let second_result = ensure_path(&mut new_scope, "PATH");
+
+            if second_result.is_some() {
+                error = error.or(first_result);
+            }
+        }
+    }
 
     if let Ok(last_overlay_name) = &stack.last_overlay_name() {
         if let Some(env_vars) = Arc::make_mut(&mut engine_state.env_vars).get_mut(last_overlay_name)
diff --git a/src/config_files.rs b/src/config_files.rs
index 3493fe0be8..ce15772e4e 100644
--- a/src/config_files.rs
+++ b/src/config_files.rs
@@ -52,6 +52,18 @@ pub(crate) fn read_config_file(
             use_color
         );
     } else {
+        let start_time = std::time::Instant::now();
+        let config = engine_state.get_config();
+        let use_color = config.use_ansi_coloring.get(engine_state);
+        if let Err(e) = convert_env_values(engine_state, stack) {
+            report_shell_error(engine_state, &e);
+        }
+        perf!(
+            "translate env vars before default_config.nu",
+            start_time,
+            use_color
+        );
+
         eval_default_config(engine_state, stack, get_default_config(), is_env_config);
     };