diff --git a/crates/file_finder/src/open_path_prompt.rs b/crates/file_finder/src/open_path_prompt.rs
index 71203874f69494..b5b29ba83693b4 100644
--- a/crates/file_finder/src/open_path_prompt.rs
+++ b/crates/file_finder/src/open_path_prompt.rs
@@ -3,7 +3,7 @@ use fuzzy::StringMatchCandidate;
 use picker::{Picker, PickerDelegate};
 use project::DirectoryLister;
 use std::{
-    path::{Path, PathBuf},
+    path::{Path, PathBuf, MAIN_SEPARATOR_STR},
     sync::{
         atomic::{self, AtomicBool},
         Arc,
@@ -40,12 +40,19 @@ impl OpenPathDelegate {
     }
 }
 
+#[derive(Debug)]
 struct DirectoryState {
     path: String,
-    match_candidates: Vec<StringMatchCandidate>,
+    match_candidates: Vec<CandidateInfo>,
     error: Option<SharedString>,
 }
 
+#[derive(Debug, Clone)]
+struct CandidateInfo {
+    path: StringMatchCandidate,
+    is_dir: bool,
+}
+
 impl OpenPathPrompt {
     pub(crate) fn register(
         workspace: &mut Workspace,
@@ -93,8 +100,6 @@ impl PickerDelegate for OpenPathDelegate {
         cx.notify();
     }
 
-    // todo(windows)
-    // Is this method woring correctly on Windows? This method uses `/` for path separator.
     fn update_matches(
         &mut self,
         query: String,
@@ -102,13 +107,26 @@ impl PickerDelegate for OpenPathDelegate {
         cx: &mut Context<Picker<Self>>,
     ) -> gpui::Task<()> {
         let lister = self.lister.clone();
-        let (mut dir, suffix) = if let Some(index) = query.rfind('/') {
-            (query[..index].to_string(), query[index + 1..].to_string())
+        let query_path = Path::new(&query);
+        let last_item = query_path
+            .file_name()
+            .unwrap_or_default()
+            .to_string_lossy()
+            .to_string();
+        let (mut dir, suffix) = if let Some(dir) = query.strip_suffix(&last_item) {
+            (dir.to_string(), last_item)
         } else {
             (query, String::new())
         };
         if dir == "" {
-            dir = "/".to_string();
+            #[cfg(not(target_os = "windows"))]
+            {
+                dir = "/".to_string();
+            }
+            #[cfg(target_os = "windows")]
+            {
+                dir = "C:\\".to_string();
+            }
         }
 
         let query = if self
@@ -134,12 +152,16 @@ impl PickerDelegate for OpenPathDelegate {
                 this.update(&mut cx, |this, _| {
                     this.delegate.directory_state = Some(match paths {
                         Ok(mut paths) => {
-                            paths.sort_by(|a, b| compare_paths((a, true), (b, true)));
+                            paths.sort_by(|a, b| compare_paths((&a.path, true), (&b.path, true)));
                             let match_candidates = paths
                                 .iter()
                                 .enumerate()
-                                .map(|(ix, path)| {
-                                    StringMatchCandidate::new(ix, &path.to_string_lossy())
+                                .map(|(ix, item)| CandidateInfo {
+                                    path: StringMatchCandidate::new(
+                                        ix,
+                                        &item.path.to_string_lossy(),
+                                    ),
+                                    is_dir: item.is_dir,
                                 })
                                 .collect::<Vec<_>>();
 
@@ -178,7 +200,7 @@ impl PickerDelegate for OpenPathDelegate {
             };
 
             if !suffix.starts_with('.') {
-                match_candidates.retain(|m| !m.string.starts_with('.'));
+                match_candidates.retain(|m| !m.path.string.starts_with('.'));
             }
 
             if suffix == "" {
@@ -186,7 +208,7 @@ impl PickerDelegate for OpenPathDelegate {
                     this.delegate.matches.clear();
                     this.delegate
                         .matches
-                        .extend(match_candidates.iter().map(|m| m.id));
+                        .extend(match_candidates.iter().map(|m| m.path.id));
 
                     cx.notify();
                 })
@@ -194,8 +216,9 @@ impl PickerDelegate for OpenPathDelegate {
                 return;
             }
 
+            let candidates = match_candidates.iter().map(|m| &m.path).collect::<Vec<_>>();
             let matches = fuzzy::match_strings(
-                match_candidates.as_slice(),
+                candidates.as_slice(),
                 &suffix,
                 false,
                 100,
@@ -217,7 +240,7 @@ impl PickerDelegate for OpenPathDelegate {
                         this.delegate.directory_state.as_ref().and_then(|d| {
                             d.match_candidates
                                 .get(*m)
-                                .map(|c| !c.string.starts_with(&suffix))
+                                .map(|c| !c.path.string.starts_with(&suffix))
                         }),
                         *m,
                     )
@@ -239,7 +262,16 @@ impl PickerDelegate for OpenPathDelegate {
                 let m = self.matches.get(self.selected_index)?;
                 let directory_state = self.directory_state.as_ref()?;
                 let candidate = directory_state.match_candidates.get(*m)?;
-                Some(format!("{}/{}", directory_state.path, candidate.string))
+                Some(format!(
+                    "{}{}{}",
+                    directory_state.path,
+                    candidate.path.string,
+                    if candidate.is_dir {
+                        MAIN_SEPARATOR_STR
+                    } else {
+                        ""
+                    }
+                ))
             })
             .unwrap_or(query),
         )
@@ -260,7 +292,7 @@ impl PickerDelegate for OpenPathDelegate {
                 .resolve_tilde(&directory_state.path, cx)
                 .as_ref(),
         )
-        .join(&candidate.string);
+        .join(&candidate.path.string);
         if let Some(tx) = self.tx.take() {
             tx.send(Some(vec![result])).ok();
         }
@@ -294,7 +326,7 @@ impl PickerDelegate for OpenPathDelegate {
                 .spacing(ListItemSpacing::Sparse)
                 .inset(true)
                 .toggle_state(selected)
-                .child(LabelLike::new().child(candidate.string.clone())),
+                .child(LabelLike::new().child(candidate.path.string.clone())),
         )
     }
 
@@ -307,6 +339,6 @@ impl PickerDelegate for OpenPathDelegate {
     }
 
     fn placeholder_text(&self, _window: &mut Window, _cx: &mut App) -> Arc<str> {
-        Arc::from("[directory/]filename.ext")
+        Arc::from(format!("[directory{MAIN_SEPARATOR_STR}]filename.ext"))
     }
 }
diff --git a/crates/fuzzy/src/matcher.rs b/crates/fuzzy/src/matcher.rs
index 66a480d87a8151..5e520eccb73295 100644
--- a/crates/fuzzy/src/matcher.rs
+++ b/crates/fuzzy/src/matcher.rs
@@ -1,5 +1,5 @@
 use std::{
-    borrow::Cow,
+    borrow::{Borrow, Cow},
     sync::atomic::{self, AtomicBool},
 };
 
@@ -50,22 +50,24 @@ impl<'a> Matcher<'a> {
 
     /// Filter and score fuzzy match candidates. Results are returned unsorted, in the same order as
     /// the input candidates.
-    pub fn match_candidates<C: MatchCandidate, R, F>(
+    pub fn match_candidates<C, R, F, T>(
         &mut self,
         prefix: &[char],
         lowercase_prefix: &[char],
-        candidates: impl Iterator<Item = C>,
+        candidates: impl Iterator<Item = T>,
         results: &mut Vec<R>,
         cancel_flag: &AtomicBool,
         build_match: F,
     ) where
+        C: MatchCandidate,
+        T: Borrow<C>,
         F: Fn(&C, f64, &Vec<usize>) -> R,
     {
         let mut candidate_chars = Vec::new();
         let mut lowercase_candidate_chars = Vec::new();
 
         for candidate in candidates {
-            if !candidate.has_chars(self.query_char_bag) {
+            if !candidate.borrow().has_chars(self.query_char_bag) {
                 continue;
             }
 
@@ -75,7 +77,7 @@ impl<'a> Matcher<'a> {
 
             candidate_chars.clear();
             lowercase_candidate_chars.clear();
-            for c in candidate.to_string().chars() {
+            for c in candidate.borrow().to_string().chars() {
                 candidate_chars.push(c);
                 lowercase_candidate_chars.append(&mut c.to_lowercase().collect::<Vec<_>>());
             }
@@ -98,7 +100,11 @@ impl<'a> Matcher<'a> {
             );
 
             if score > 0.0 {
-                results.push(build_match(&candidate, score, &self.match_positions));
+                results.push(build_match(
+                    candidate.borrow(),
+                    score,
+                    &self.match_positions,
+                ));
             }
         }
     }
diff --git a/crates/fuzzy/src/strings.rs b/crates/fuzzy/src/strings.rs
index 458278739ab2a8..419127ed6e6cac 100644
--- a/crates/fuzzy/src/strings.rs
+++ b/crates/fuzzy/src/strings.rs
@@ -4,7 +4,7 @@ use crate::{
 };
 use gpui::BackgroundExecutor;
 use std::{
-    borrow::Cow,
+    borrow::{Borrow, Cow},
     cmp::{self, Ordering},
     iter,
     ops::Range,
@@ -113,14 +113,17 @@ impl Ord for StringMatch {
     }
 }
 
-pub async fn match_strings(
-    candidates: &[StringMatchCandidate],
+pub async fn match_strings<T>(
+    candidates: &[T],
     query: &str,
     smart_case: bool,
     max_results: usize,
     cancel_flag: &AtomicBool,
     executor: BackgroundExecutor,
-) -> Vec<StringMatch> {
+) -> Vec<StringMatch>
+where
+    T: Borrow<StringMatchCandidate> + Sync,
+{
     if candidates.is_empty() || max_results == 0 {
         return Default::default();
     }
@@ -129,10 +132,10 @@ pub async fn match_strings(
         return candidates
             .iter()
             .map(|candidate| StringMatch {
-                candidate_id: candidate.id,
+                candidate_id: candidate.borrow().id,
                 score: 0.,
                 positions: Default::default(),
-                string: candidate.string.clone(),
+                string: candidate.borrow().string.clone(),
             })
             .collect();
     }
@@ -163,10 +166,12 @@ pub async fn match_strings(
                     matcher.match_candidates(
                         &[],
                         &[],
-                        candidates[segment_start..segment_end].iter(),
+                        candidates[segment_start..segment_end]
+                            .iter()
+                            .map(|c| c.borrow()),
                         results,
                         cancel_flag,
-                        |candidate, score, positions| StringMatch {
+                        |candidate: &&StringMatchCandidate, score, positions| StringMatch {
                             candidate_id: candidate.id,
                             score,
                             positions: positions.clone(),
diff --git a/crates/project/src/project.rs b/crates/project/src/project.rs
index 7d51fbc9c69ec1..10c0e80e2747b1 100644
--- a/crates/project/src/project.rs
+++ b/crates/project/src/project.rs
@@ -524,6 +524,12 @@ enum EntitySubscription {
     SettingsObserver(PendingEntitySubscription<SettingsObserver>),
 }
 
+#[derive(Debug, Clone)]
+pub struct DirectoryItem {
+    pub path: PathBuf,
+    pub is_dir: bool,
+}
+
 #[derive(Clone)]
 pub enum DirectoryLister {
     Project(Entity<Project>),
@@ -552,10 +558,10 @@ impl DirectoryLister {
                 return worktree.read(cx).abs_path().to_string_lossy().to_string();
             }
         };
-        "~/".to_string()
+        format!("~{}", std::path::MAIN_SEPARATOR_STR)
     }
 
-    pub fn list_directory(&self, path: String, cx: &mut App) -> Task<Result<Vec<PathBuf>>> {
+    pub fn list_directory(&self, path: String, cx: &mut App) -> Task<Result<Vec<DirectoryItem>>> {
         match self {
             DirectoryLister::Project(project) => {
                 project.update(cx, |project, cx| project.list_directory(path, cx))
@@ -568,8 +574,12 @@ impl DirectoryLister {
                     let query = Path::new(expanded.as_ref());
                     let mut response = fs.read_dir(query).await?;
                     while let Some(path) = response.next().await {
-                        if let Some(file_name) = path?.file_name() {
-                            results.push(PathBuf::from(file_name.to_os_string()));
+                        let path = path?;
+                        if let Some(file_name) = path.file_name() {
+                            results.push(DirectoryItem {
+                                path: PathBuf::from(file_name.to_os_string()),
+                                is_dir: fs.is_dir(&path).await,
+                            });
                         }
                     }
                     Ok(results)
@@ -3479,7 +3489,7 @@ impl Project {
         &self,
         query: String,
         cx: &mut Context<Self>,
-    ) -> Task<Result<Vec<PathBuf>>> {
+    ) -> Task<Result<Vec<DirectoryItem>>> {
         if self.is_local() {
             DirectoryLister::Local(self.fs.clone()).list_directory(query, cx)
         } else if let Some(session) = self.ssh_client.as_ref() {
@@ -3487,12 +3497,23 @@ impl Project {
             let request = proto::ListRemoteDirectory {
                 dev_server_id: SSH_PROJECT_ID,
                 path: path_buf.to_proto(),
+                config: Some(proto::ListRemoteDirectoryConfig { is_dir: true }),
             };
 
             let response = session.read(cx).proto_client().request(request);
             cx.background_spawn(async move {
-                let response = response.await?;
-                Ok(response.entries.into_iter().map(PathBuf::from).collect())
+                let proto::ListRemoteDirectoryResponse {
+                    entries,
+                    entry_info,
+                } = response.await?;
+                Ok(entries
+                    .into_iter()
+                    .zip(entry_info)
+                    .map(|(entry, info)| DirectoryItem {
+                        path: PathBuf::from(entry),
+                        is_dir: info.is_dir,
+                    })
+                    .collect())
             })
         } else {
             Task::ready(Err(anyhow!("cannot list directory in remote project")))
diff --git a/crates/proto/proto/zed.proto b/crates/proto/proto/zed.proto
index 2a708a7e31fe34..c9037342fd0fa2 100644
--- a/crates/proto/proto/zed.proto
+++ b/crates/proto/proto/zed.proto
@@ -561,13 +561,23 @@ message JoinProject {
     uint64 project_id = 1;
 }
 
+message ListRemoteDirectoryConfig {
+    bool is_dir = 1;
+}
+
 message ListRemoteDirectory {
     uint64 dev_server_id = 1;
     string path = 2;
+    ListRemoteDirectoryConfig config = 3;
+}
+
+message EntryInfo {
+    bool is_dir = 1;
 }
 
 message ListRemoteDirectoryResponse {
     repeated string entries = 1;
+    repeated EntryInfo entry_info = 2;
 }
 
 message JoinProjectResponse {
diff --git a/crates/remote_server/src/headless_project.rs b/crates/remote_server/src/headless_project.rs
index 4f09647e17cc00..fadd603b502f20 100644
--- a/crates/remote_server/src/headless_project.rs
+++ b/crates/remote_server/src/headless_project.rs
@@ -554,15 +554,29 @@ impl HeadlessProject {
     ) -> Result<proto::ListRemoteDirectoryResponse> {
         let fs = cx.read_entity(&this, |this, _| this.fs.clone())?;
         let expanded = PathBuf::from_proto(shellexpand::tilde(&envelope.payload.path).to_string());
+        let check_info = envelope
+            .payload
+            .config
+            .as_ref()
+            .is_some_and(|config| config.is_dir);
 
         let mut entries = Vec::new();
+        let mut entry_info = Vec::new();
         let mut response = fs.read_dir(&expanded).await?;
         while let Some(path) = response.next().await {
-            if let Some(file_name) = path?.file_name() {
+            let path = path?;
+            if let Some(file_name) = path.file_name() {
                 entries.push(file_name.to_string_lossy().to_string());
+                if check_info {
+                    let is_dir = fs.is_dir(&path).await;
+                    entry_info.push(proto::EntryInfo { is_dir });
+                }
             }
         }
-        Ok(proto::ListRemoteDirectoryResponse { entries })
+        Ok(proto::ListRemoteDirectoryResponse {
+            entries,
+            entry_info,
+        })
     }
 
     pub async fn handle_get_path_metadata(