diff --git a/crates/nu-command/src/filesystem/start.rs b/crates/nu-command/src/filesystem/start.rs
index 790315a94a..5e96ffa568 100644
--- a/crates/nu-command/src/filesystem/start.rs
+++ b/crates/nu-command/src/filesystem/start.rs
@@ -1,11 +1,15 @@
+use itertools::Itertools;
+use nu_engine::env_to_strings;
 use nu_engine::CallExt;
 use nu_path::canonicalize_with;
 use nu_protocol::ast::Call;
 use nu_protocol::engine::{Command, EngineState, Stack};
 use nu_protocol::{
-    Category, Example, PipelineData, ShellError, Signature, Spanned, SyntaxShape, Type,
+    Category, Example, PipelineData, ShellError, Signature, Span, Spanned, SyntaxShape, Type,
 };
+use std::ffi::{OsStr, OsString};
 use std::path::Path;
+use std::process::Stdio;
 
 #[derive(Clone)]
 pub struct Start;
@@ -46,7 +50,7 @@ impl Command for Start {
         // only check if file exists in current current directory
         let file_path = Path::new(path_no_whitespace);
         if file_path.exists() {
-            open::that(path_no_whitespace)?;
+            open_path(path_no_whitespace, engine_state, stack, path.span)?;
         } else if file_path.starts_with("https://") || file_path.starts_with("http://") {
             let url = url::Url::parse(&path.item).map_err(|_| {
                 ShellError::GenericError(
@@ -57,13 +61,13 @@ impl Command for Start {
                     Vec::new(),
                 )
             })?;
-            open::that(url.as_str())?;
+            open_path(url.as_str(), engine_state, stack, path.span)?;
         } else {
             // try to distinguish between file not found and opening url without prefix
-            if let Ok(path) =
+            if let Ok(canon_path) =
                 canonicalize_with(path_no_whitespace, std::env::current_dir()?.as_path())
             {
-                open::that(path)?;
+                open_path(canon_path, engine_state, stack, path.span)?;
             } else {
                 // open crate does not allow opening URL without prefix
                 let path_with_prefix = Path::new("https://").join(&path.item);
@@ -83,7 +87,7 @@ impl Command for Start {
                         let ext = Path::new(&domain).extension().and_then(|s| s.to_str());
                         if let Some(url_ext) = ext {
                             if common_domains.contains(&url_ext) {
-                                open::that(url.as_str())?;
+                                open_path(url.as_str(), engine_state, stack, path.span)?;
                             }
                         }
                     }
@@ -130,3 +134,65 @@ impl Command for Start {
         ]
     }
 }
+
+fn open_path(
+    path: impl AsRef<OsStr>,
+    engine_state: &EngineState,
+    stack: &Stack,
+    span: Span,
+) -> Result<(), ShellError> {
+    try_commands(open::commands(path), engine_state, stack, span)
+}
+
+fn try_commands(
+    commands: Vec<std::process::Command>,
+    engine_state: &EngineState,
+    stack: &Stack,
+    span: Span,
+) -> Result<(), ShellError> {
+    let env_vars_str = env_to_strings(engine_state, stack)?;
+    commands
+        .into_iter()
+        .map(|mut cmd| {
+            let status = cmd
+                .envs(&env_vars_str)
+                .stdin(Stdio::null())
+                .stdout(Stdio::null())
+                .stderr(Stdio::null())
+                .status();
+            match status {
+                Ok(status) if status.success() => Ok(()),
+                Ok(status) => Err(format!(
+                    "\nCommand `{}` failed with {}",
+                    format_command(&cmd),
+                    status
+                )),
+                Err(err) => Err(format!(
+                    "\nCommand `{}` failed with {}",
+                    format_command(&cmd),
+                    err
+                )),
+            }
+        })
+        .take_while_inclusive(|result| result.is_err())
+        .fold(Err("".to_string()), |combined_result, next_result| {
+            combined_result.or_else(|combined_message| {
+                next_result.map_err(|next_message| combined_message + &next_message)
+            })
+        })
+        .map_err(|message| ShellError::ExternalCommand {
+            label: "No command found to start with this path".to_string(),
+            help: "Try different path or install appropriate command\n".to_string() + &message,
+            span,
+        })
+}
+
+fn format_command(command: &std::process::Command) -> String {
+    let parts_iter = std::iter::repeat(command.get_program())
+        .take(1)
+        .chain(command.get_args());
+    Itertools::intersperse(parts_iter, " ".as_ref())
+        .collect::<OsString>()
+        .to_string_lossy()
+        .into_owned()
+}