diff --git a/cli/src/cli_util.rs b/cli/src/cli_util.rs
index 42782313a8..32cc17c5cb 100644
--- a/cli/src/cli_util.rs
+++ b/cli/src/cli_util.rs
@@ -69,7 +69,7 @@ use jj_lib::working_copy::{
 use jj_lib::workspace::{
     default_working_copy_factories, LockedWorkspace, Workspace, WorkspaceLoadError, WorkspaceLoader,
 };
-use jj_lib::{dag_walk, file_util, git, op_heads_store, op_walk, revset};
+use jj_lib::{dag_walk, file_util, fileset, git, op_heads_store, op_walk, revset};
 use once_cell::unsync::OnceCell;
 use tracing::instrument;
 use tracing_chrome::ChromeLayerBuilder;
@@ -657,10 +657,7 @@ impl WorkspaceCommandHelper {
         if values.is_empty() {
             Ok(FilesetExpression::all())
         } else {
-            let ctx = FilesetParseContext {
-                cwd: &self.cwd,
-                workspace_root: self.workspace.workspace_root(),
-            };
+            let ctx = self.fileset_parse_context();
             let expressions = values
                 .iter()
                 .map(|v| FilePattern::parse(&ctx, v))
@@ -671,6 +668,26 @@ impl WorkspaceCommandHelper {
         }
     }
 
+    /// Parses the given fileset expressions and concatenates them all.
+    pub fn parse_union_filesets(
+        &self,
+        file_args: &[String], // TODO: introduce FileArg newtype?
+    ) -> Result<FilesetExpression, CommandError> {
+        let ctx = self.fileset_parse_context();
+        let expressions: Vec<_> = file_args
+            .iter()
+            .map(|arg| fileset::parse(arg, &ctx))
+            .try_collect()?;
+        Ok(FilesetExpression::union_all(expressions))
+    }
+
+    pub(crate) fn fileset_parse_context(&self) -> FilesetParseContext<'_> {
+        FilesetParseContext {
+            cwd: &self.cwd,
+            workspace_root: self.workspace.workspace_root(),
+        }
+    }
+
     #[instrument(skip_all)]
     pub fn base_ignores(&self) -> Result<Arc<GitIgnoreFile>, GitIgnoreError> {
         fn get_excludes_file_path(config: &gix::config::File) -> Option<PathBuf> {
diff --git a/cli/src/command_error.rs b/cli/src/command_error.rs
index 5be11648e6..c9121e85c5 100644
--- a/cli/src/command_error.rs
+++ b/cli/src/command_error.rs
@@ -19,6 +19,7 @@ use std::{error, io, iter, str};
 
 use itertools::Itertools as _;
 use jj_lib::backend::BackendError;
+use jj_lib::fileset::{FilesetParseError, FilesetParseErrorKind};
 use jj_lib::git::{GitConfigParseError, GitExportError, GitImportError, GitRemoteManagementError};
 use jj_lib::gitignore::GitIgnoreError;
 use jj_lib::op_heads_store::OpHeadResolutionError;
@@ -400,6 +401,24 @@ impl From<RevsetEvaluationError> for CommandError {
     }
 }
 
+impl From<FilesetParseError> for CommandError {
+    fn from(err: FilesetParseError) -> Self {
+        let hint = match err.kind() {
+            FilesetParseErrorKind::NoSuchFunction {
+                name: _,
+                candidates,
+            } => format_similarity_hint(candidates),
+            FilesetParseErrorKind::InvalidArguments { .. }
+            | FilesetParseErrorKind::Expression(_) => find_source_parse_error_hint(&err),
+            _ => None,
+        };
+        let mut cmd_err =
+            user_error_with_message(format!("Failed to parse fileset: {}", err.kind()), err);
+        cmd_err.extend_hints(hint);
+        cmd_err
+    }
+}
+
 impl From<RevsetParseError> for CommandError {
     fn from(err: RevsetParseError) -> Self {
         // Only for the bottom error, which is usually the root cause
diff --git a/cli/src/commands/debug.rs b/cli/src/commands/debug.rs
index 7916503191..1b22cc96de 100644
--- a/cli/src/commands/debug.rs
+++ b/cli/src/commands/debug.rs
@@ -25,7 +25,7 @@ use jj_lib::object_id::ObjectId;
 use jj_lib::repo::Repo;
 use jj_lib::repo_path::RepoPathBuf;
 use jj_lib::working_copy::WorkingCopy;
-use jj_lib::{op_walk, revset};
+use jj_lib::{fileset, op_walk, revset};
 
 use crate::cli_util::{CommandHelper, RevisionArg};
 use crate::command_error::{internal_error, user_error, CommandError};
@@ -36,6 +36,7 @@ use crate::{revset_util, template_parser};
 #[derive(Subcommand, Clone, Debug)]
 #[command(hide = true)]
 pub enum DebugCommand {
+    Fileset(DebugFilesetArgs),
     Revset(DebugRevsetArgs),
     #[command(name = "workingcopy")]
     WorkingCopy(DebugWorkingCopyArgs),
@@ -50,6 +51,13 @@ pub enum DebugCommand {
     Watchman(DebugWatchmanSubcommand),
 }
 
+/// Parse fileset expression
+#[derive(clap::Args, Clone, Debug)]
+pub struct DebugFilesetArgs {
+    #[arg(value_hint = clap::ValueHint::AnyPath)]
+    path: String,
+}
+
 /// Evaluate revset to full commit IDs
 #[derive(clap::Args, Clone, Debug)]
 pub struct DebugRevsetArgs {
@@ -121,6 +129,7 @@ pub fn cmd_debug(
     subcommand: &DebugCommand,
 ) -> Result<(), CommandError> {
     match subcommand {
+        DebugCommand::Fileset(args) => cmd_debug_fileset(ui, command, args),
         DebugCommand::Revset(args) => cmd_debug_revset(ui, command, args),
         DebugCommand::WorkingCopy(args) => cmd_debug_working_copy(ui, command, args),
         DebugCommand::Template(args) => cmd_debug_template(ui, command, args),
@@ -132,6 +141,25 @@ pub fn cmd_debug(
     }
 }
 
+fn cmd_debug_fileset(
+    ui: &mut Ui,
+    command: &CommandHelper,
+    args: &DebugFilesetArgs,
+) -> Result<(), CommandError> {
+    let workspace_command = command.workspace_helper(ui)?;
+    let ctx = workspace_command.fileset_parse_context();
+
+    let expression = fileset::parse(&args.path, &ctx)?;
+    writeln!(ui.stdout(), "-- Parsed:")?;
+    writeln!(ui.stdout(), "{expression:#?}")?;
+    writeln!(ui.stdout())?;
+
+    let matcher = expression.to_matcher();
+    writeln!(ui.stdout(), "-- Matcher:")?;
+    writeln!(ui.stdout(), "{matcher:#?}")?;
+    Ok(())
+}
+
 fn cmd_debug_revset(
     ui: &mut Ui,
     command: &CommandHelper,
diff --git a/cli/tests/test_debug_command.rs b/cli/tests/test_debug_command.rs
index ef8eabfd2b..4a126c3155 100644
--- a/cli/tests/test_debug_command.rs
+++ b/cli/tests/test_debug_command.rs
@@ -17,6 +17,36 @@ use regex::Regex;
 
 use crate::common::TestEnvironment;
 
+#[test]
+fn test_debug_fileset() {
+    let test_env = TestEnvironment::default();
+    test_env.jj_cmd_ok(test_env.env_root(), &["git", "init", "repo"]);
+    let workspace_path = test_env.env_root().join("repo");
+
+    let stdout = test_env.jj_cmd_success(&workspace_path, &["debug", "fileset", "all()"]);
+    assert_snapshot!(stdout, @r###"
+    -- Parsed:
+    All
+
+    -- Matcher:
+    EverythingMatcher
+    "###);
+
+    let stderr = test_env.jj_cmd_failure(&workspace_path, &["debug", "fileset", "cwd:.."]);
+    assert_snapshot!(stderr.replace('\\', "/"), @r###"
+    Error: Failed to parse fileset: Invalid file pattern
+    Caused by:
+    1:  --> 1:1
+      |
+    1 | cwd:..
+      | ^----^
+      |
+      = Invalid file pattern
+    2: Path ".." is not in the repo "."
+    3: Invalid component ".." in repo-relative path "../"
+    "###);
+}
+
 #[test]
 fn test_debug_revset() {
     let test_env = TestEnvironment::default();