diff --git a/crates/vite_task/src/lib.rs b/crates/vite_task/src/lib.rs
index a20687c3..6f473cb5 100644
--- a/crates/vite_task/src/lib.rs
+++ b/crates/vite_task/src/lib.rs
@@ -5,7 +5,9 @@ pub mod session;
 
 // Public exports for vite_task_bin
 pub use cli::{CacheSubcommand, Command, RunCommand, RunFlags};
-pub use session::{CommandHandler, ExitStatus, HandledCommand, Session, SessionConfig};
+pub use session::{
+    CommandHandler, ExitStatus, HandledCommand, Session, SessionConfig, TaskErrorHints,
+};
 pub use vite_task_graph::{
     config::{
         self,
diff --git a/crates/vite_task/src/session/mod.rs b/crates/vite_task/src/session/mod.rs
index c378794f..abeb11da 100644
--- a/crates/vite_task/src/session/mod.rs
+++ b/crates/vite_task/src/session/mod.rs
@@ -4,12 +4,18 @@ mod execute;
 pub(crate) mod reporter;
 
 // Re-export types that are part of the public API
-use std::{ffi::OsStr, fmt::Debug, io::IsTerminal, sync::Arc};
+use std::{
+    ffi::OsStr,
+    fmt::Debug,
+    io::{IsTerminal, Write as _},
+    sync::Arc,
+};
 
 use cache::ExecutionCache;
 pub use cache::{CacheMiss, FingerprintMismatch};
 use clap::Parser as _;
 use once_cell::sync::OnceCell;
+use owo_colors::{OwoColorize as _, Stream, Style};
 pub use reporter::ExitStatus;
 use reporter::{
     GroupedReporterBuilder, InterleavedReporterBuilder, LabeledReporterBuilder,
@@ -80,6 +86,11 @@ impl TaskGraphLoader for LazyTaskGraph<'_> {
     }
 }
 
+pub struct TaskErrorHints {
+    pub task_list_hint: Str,
+    pub task_source_hint: Str,
+}
+
 pub struct SessionConfig<'a> {
     pub command_handler: &'a mut (dyn CommandHandler + 'a),
     pub user_config_loader: &'a mut (dyn UserConfigLoader + 'a),
@@ -110,6 +121,9 @@ pub trait CommandHandler: Debug {
         &mut self,
         command: &mut ScriptCommand,
     ) -> anyhow::Result<HandledCommand>;
+
+    /// Returns hints shown to the user when a task is not found.
+    fn task_error_hints(&self) -> TaskErrorHints;
 }
 
 #[derive(derive_more::Debug)]
@@ -165,6 +179,7 @@ pub struct Session<'a> {
     plan_request_parser: PlanRequestParser<'a>,
 
     program_name: Str,
+    task_error_hints: TaskErrorHints,
 
     /// Cache is lazily initialized to avoid `SQLite` race conditions when multiple
     /// processes (e.g., parallel `vt lib` commands) start simultaneously.
@@ -227,6 +242,7 @@ impl<'a> Session<'a> {
         prepend_path_env(&mut envs, &workspace_node_modules_bin)?;
 
         // Cache is lazily initialized on first access to avoid SQLite race conditions
+        let task_error_hints = config.command_handler.task_error_hints();
         Ok(Self {
             workspace_path: Arc::clone(&workspace_root.path),
             lazy_task_graph: LazyTaskGraph::Uninitialized {
@@ -237,6 +253,7 @@ impl<'a> Session<'a> {
             cwd,
             plan_request_parser: PlanRequestParser { command_handler: config.command_handler },
             program_name: config.program_name,
+            task_error_hints,
             cache: OnceCell::new(),
             cache_path,
         })
@@ -246,13 +263,17 @@ impl<'a> Session<'a> {
     ///
     /// # Errors
     ///
-    /// Returns an error if planning or execution fails.
+    /// Prints user-facing CLI errors and returns an exit status.
     #[tracing::instrument(level = "debug", skip_all)]
-    pub async fn main(mut self, command: Command) -> anyhow::Result<ExitStatus> {
+    pub async fn main(mut self, command: Command) -> ExitStatus {
+        let verbose = matches!(&command, Command::Run(run) if run.flags.verbose);
         match self.main_inner(command).await {
-            Ok(()) => Ok(ExitStatus::SUCCESS),
-            Err(SessionError::EarlyExit(status)) => Ok(status),
-            Err(SessionError::Anyhow(err)) => Err(err),
+            Ok(()) => ExitStatus::SUCCESS,
+            Err(SessionError::EarlyExit(status)) => status,
+            Err(SessionError::Anyhow(err)) => {
+                self.print_cli_error(&err, verbose);
+                ExitStatus::FAILURE
+            }
         }
     }
 
@@ -343,6 +364,87 @@ impl<'a> Session<'a> {
         Ok(())
     }
 
+    fn print_cli_error(&self, err: &anyhow::Error, verbose: bool) {
+        let mut stderr = std::io::stderr();
+
+        if let Some(plan_error) = err.downcast_ref::<vite_task_plan::Error>() {
+            if let Some(nested) = plan_error.nested_missing_task() {
+                let _ = writeln!(
+                    stderr,
+                    "{}",
+                    vite_str::format!("Task \"{}\" not found.", nested.task_name)
+                        .if_supports_color(Stream::Stderr, |text| {
+                            text.style(Style::new().red().bold())
+                        })
+                );
+                let _ = writeln!(
+                    stderr,
+                    "{} depends on \"{}\" via `{}`.",
+                    nested.parent_task, nested.task_name, nested.command
+                );
+                let _ = writeln!(stderr, "Next steps:");
+                let _ = writeln!(stderr, "  {}", self.task_error_hints.task_list_hint);
+                let _ = writeln!(stderr, "  {}", self.task_error_hints.task_source_hint);
+                if verbose {
+                    let _ = writeln!(stderr);
+                    let _ = writeln!(
+                        stderr,
+                        "{}",
+                        "Raw details:".if_supports_color(Stream::Stderr, |text| text.bold())
+                    );
+                    let _ = writeln!(stderr, "{err:#}");
+                    let _ = writeln!(stderr, "Exit code: {}", ExitStatus::FAILURE.0);
+                }
+                let _ = stderr.flush();
+                return;
+            }
+
+            if let vite_task_plan::Error::NoTasksMatched(task_name) = plan_error {
+                let _ = writeln!(
+                    stderr,
+                    "{}",
+                    vite_str::format!("Task \"{}\" not found.", task_name)
+                        .if_supports_color(Stream::Stderr, |text| text
+                            .style(Style::new().red().bold()))
+                );
+                let _ = writeln!(stderr, "Next steps:");
+                let _ = writeln!(stderr, "  {}", self.task_error_hints.task_list_hint);
+                let _ = writeln!(stderr, "  {}", self.task_error_hints.task_source_hint);
+                if verbose {
+                    let _ = writeln!(stderr);
+                    let _ = writeln!(
+                        stderr,
+                        "{}",
+                        "Raw details:".if_supports_color(Stream::Stderr, |text| text.bold())
+                    );
+                    let _ = writeln!(stderr, "{err:#}");
+                    let _ = writeln!(stderr, "Exit code: {}", ExitStatus::FAILURE.0);
+                }
+                let _ = stderr.flush();
+                return;
+            }
+        }
+
+        let _ = writeln!(
+            stderr,
+            "{} {}",
+            "✗".if_supports_color(Stream::Stderr, |text| text.style(Style::new().red().bold())),
+            err.to_string()
+                .if_supports_color(Stream::Stderr, |text| text.style(Style::new().red()))
+        );
+        if verbose {
+            let _ = writeln!(stderr);
+            let _ = writeln!(
+                stderr,
+                "{}",
+                "Raw details:".if_supports_color(Stream::Stderr, |text| text.bold())
+            );
+            let _ = writeln!(stderr, "{err:#}");
+            let _ = writeln!(stderr, "Exit code: {}", ExitStatus::FAILURE.0);
+        }
+        let _ = stderr.flush();
+    }
+
     /// Show the task selector or list, and return a plan request for the selected task.
     ///
     /// In interactive mode, shows a fuzzy-searchable selection list. On selection,
diff --git a/crates/vite_task_bin/src/lib.rs b/crates/vite_task_bin/src/lib.rs
index 32dc72f3..dc495ea0 100644
--- a/crates/vite_task_bin/src/lib.rs
+++ b/crates/vite_task_bin/src/lib.rs
@@ -9,8 +9,8 @@ use clap::Parser;
 use vite_path::AbsolutePath;
 use vite_str::Str;
 use vite_task::{
-    Command, EnabledCacheConfig, HandledCommand, ScriptCommand, SessionConfig, UserCacheConfig,
-    get_path_env, plan_request::SyntheticPlanRequest,
+    Command, EnabledCacheConfig, HandledCommand, ScriptCommand, SessionConfig, TaskErrorHints,
+    UserCacheConfig, get_path_env, plan_request::SyntheticPlanRequest,
 };
 
 #[derive(Debug, Default)]
@@ -105,6 +105,15 @@ impl vite_task::CommandHandler for CommandHandler {
             Args::Task(parsed) => Ok(HandledCommand::ViteTaskCommand(parsed)),
         }
     }
+
+    fn task_error_hints(&self) -> TaskErrorHints {
+        TaskErrorHints {
+            task_list_hint: Str::from("Run `vt run` to browse available tasks."),
+            task_source_hint: Str::from(
+                "Check `vite-task.json` and `package.json` scripts where tasks are defined.",
+            ),
+        }
+    }
 }
 
 /// A `UserConfigLoader` implementation that only loads `vite-task.json`.
diff --git a/crates/vite_task_bin/src/main.rs b/crates/vite_task_bin/src/main.rs
index a0569897..e268d6f8 100644
--- a/crates/vite_task_bin/src/main.rs
+++ b/crates/vite_task_bin/src/main.rs
@@ -14,5 +14,5 @@ async fn run() -> anyhow::Result<ExitStatus> {
     let args = Command::parse();
     let mut owned_config = OwnedSessionConfig::default();
     let session = Session::init(owned_config.as_config())?;
-    session.main(args).await
+    Ok(session.main(args).await)
 }
diff --git a/crates/vite_task_bin/tests/e2e_snapshots/fixtures/error_cycle_dependency/snapshots/cycle dependency error.snap b/crates/vite_task_bin/tests/e2e_snapshots/fixtures/error_cycle_dependency/snapshots/cycle dependency error.snap
index 94bfc0dd..1762fe65 100644
--- a/crates/vite_task_bin/tests/e2e_snapshots/fixtures/error_cycle_dependency/snapshots/cycle dependency error.snap	
+++ b/crates/vite_task_bin/tests/e2e_snapshots/fixtures/error_cycle_dependency/snapshots/cycle dependency error.snap	
@@ -3,4 +3,4 @@ source: crates/vite_task_bin/tests/e2e_snapshots/main.rs
 expression: e2e_outputs
 ---
 [1]> vt run task-a # task-a -> task-b -> task-a cycle
-Error: Cycle dependency detected: error-cycle-dependency-test#task-a -> error-cycle-dependency-test#task-b -> error-cycle-dependency-test#task-a
+✗ Cycle dependency detected: error-cycle-dependency-test#task-a -> error-cycle-dependency-test#task-b -> error-cycle-dependency-test#task-a
diff --git a/crates/vite_task_bin/tests/e2e_snapshots/fixtures/nested-task-not-found/package.json b/crates/vite_task_bin/tests/e2e_snapshots/fixtures/nested-task-not-found/package.json
new file mode 100644
index 00000000..9d59d9eb
--- /dev/null
+++ b/crates/vite_task_bin/tests/e2e_snapshots/fixtures/nested-task-not-found/package.json
@@ -0,0 +1,5 @@
+{
+  "name": "nested-task-not-found-test",
+  "private": true,
+  "workspaces": []
+}
diff --git a/crates/vite_task_bin/tests/e2e_snapshots/fixtures/nested-task-not-found/snapshots.toml b/crates/vite_task_bin/tests/e2e_snapshots/fixtures/nested-task-not-found/snapshots.toml
new file mode 100644
index 00000000..e432bfad
--- /dev/null
+++ b/crates/vite_task_bin/tests/e2e_snapshots/fixtures/nested-task-not-found/snapshots.toml
@@ -0,0 +1,7 @@
+[[e2e]]
+name = "nested task not found"
+steps = ["vt run repro"]
+
+[[e2e]]
+name = "nested task not found verbose"
+steps = ["vt run repro --verbose"]
diff --git a/crates/vite_task_bin/tests/e2e_snapshots/fixtures/nested-task-not-found/snapshots/nested task not found verbose.snap b/crates/vite_task_bin/tests/e2e_snapshots/fixtures/nested-task-not-found/snapshots/nested task not found verbose.snap
new file mode 100644
index 00000000..eae0d8fe
--- /dev/null
+++ b/crates/vite_task_bin/tests/e2e_snapshots/fixtures/nested-task-not-found/snapshots/nested task not found verbose.snap	
@@ -0,0 +1,10 @@
+---
+source: crates/vite_task_bin/tests/e2e_snapshots/main.rs
+expression: e2e_outputs
+---
+[1]> vt run repro --verbose
+Task "missing-task" not found.
+nested-task-not-found-test#repro depends on "missing-task" via `vt run missing-task`.
+Next steps:
+  Run `vt run` to browse available tasks.
+  Check `vite-task.json` and `package.json` scripts where tasks are defined.
diff --git a/crates/vite_task_bin/tests/e2e_snapshots/fixtures/nested-task-not-found/snapshots/nested task not found.snap b/crates/vite_task_bin/tests/e2e_snapshots/fixtures/nested-task-not-found/snapshots/nested task not found.snap
new file mode 100644
index 00000000..691d462b
--- /dev/null
+++ b/crates/vite_task_bin/tests/e2e_snapshots/fixtures/nested-task-not-found/snapshots/nested task not found.snap	
@@ -0,0 +1,10 @@
+---
+source: crates/vite_task_bin/tests/e2e_snapshots/main.rs
+expression: e2e_outputs
+---
+[1]> vt run repro
+Task "missing-task" not found.
+nested-task-not-found-test#repro depends on "missing-task" via `vt run missing-task`.
+Next steps:
+  Run `vt run` to browse available tasks.
+  Check `vite-task.json` and `package.json` scripts where tasks are defined.
diff --git a/crates/vite_task_bin/tests/e2e_snapshots/fixtures/nested-task-not-found/vite-task.json b/crates/vite_task_bin/tests/e2e_snapshots/fixtures/nested-task-not-found/vite-task.json
new file mode 100644
index 00000000..277e0b62
--- /dev/null
+++ b/crates/vite_task_bin/tests/e2e_snapshots/fixtures/nested-task-not-found/vite-task.json
@@ -0,0 +1,7 @@
+{
+  "tasks": {
+    "repro": {
+      "command": "vt run missing-task"
+    }
+  }
+}
diff --git a/crates/vite_task_bin/tests/e2e_snapshots/fixtures/task-select/snapshots/non-interactive recursive typo errors.snap b/crates/vite_task_bin/tests/e2e_snapshots/fixtures/task-select/snapshots/non-interactive recursive typo errors.snap
index bcc3c8ec..32424571 100644
--- a/crates/vite_task_bin/tests/e2e_snapshots/fixtures/task-select/snapshots/non-interactive recursive typo errors.snap	
+++ b/crates/vite_task_bin/tests/e2e_snapshots/fixtures/task-select/snapshots/non-interactive recursive typo errors.snap	
@@ -3,4 +3,7 @@ source: crates/vite_task_bin/tests/e2e_snapshots/main.rs
 expression: e2e_outputs
 ---
 [1]> echo '' | vt run -r buid
-Error: Task "buid" not found
+Task "buid" not found.
+Next steps:
+  Run `vt run` to browse available tasks.
+  Check `vite-task.json` and `package.json` scripts where tasks are defined.
diff --git a/crates/vite_task_bin/tests/e2e_snapshots/fixtures/task-select/snapshots/recursive without task errors.snap b/crates/vite_task_bin/tests/e2e_snapshots/fixtures/task-select/snapshots/recursive without task errors.snap
index cfa41815..8a6cb58d 100644
--- a/crates/vite_task_bin/tests/e2e_snapshots/fixtures/task-select/snapshots/recursive without task errors.snap	
+++ b/crates/vite_task_bin/tests/e2e_snapshots/fixtures/task-select/snapshots/recursive without task errors.snap	
@@ -5,4 +5,4 @@ info:
   cwd: packages/app
 ---
 [1]> vt run -r
-Error: No task specifier provided for 'run' command
+✗ No task specifier provided for 'run' command
diff --git a/crates/vite_task_bin/tests/e2e_snapshots/fixtures/task-select/snapshots/transitive typo errors.snap b/crates/vite_task_bin/tests/e2e_snapshots/fixtures/task-select/snapshots/transitive typo errors.snap
index 246cdb0a..210a44d2 100644
--- a/crates/vite_task_bin/tests/e2e_snapshots/fixtures/task-select/snapshots/transitive typo errors.snap	
+++ b/crates/vite_task_bin/tests/e2e_snapshots/fixtures/task-select/snapshots/transitive typo errors.snap	
@@ -5,4 +5,7 @@ info:
   cwd: packages/app
 ---
 [1]> vt run -t buid
-Error: Task "buid" not found
+Task "buid" not found.
+Next steps:
+  Run `vt run` to browse available tasks.
+  Check `vite-task.json` and `package.json` scripts where tasks are defined.
diff --git a/crates/vite_task_bin/tests/e2e_snapshots/fixtures/task-select/snapshots/typo in task script fails without list.snap b/crates/vite_task_bin/tests/e2e_snapshots/fixtures/task-select/snapshots/typo in task script fails without list.snap
index 271b5f50..6acbdd4a 100644
--- a/crates/vite_task_bin/tests/e2e_snapshots/fixtures/task-select/snapshots/typo in task script fails without list.snap	
+++ b/crates/vite_task_bin/tests/e2e_snapshots/fixtures/task-select/snapshots/typo in task script fails without list.snap	
@@ -3,7 +3,8 @@ source: crates/vite_task_bin/tests/e2e_snapshots/main.rs
 expression: e2e_outputs
 ---
 [1]> vt run run-typo-task
-Error: Failed to plan tasks from `vt run nonexistent-xyz` in task task-select-test#run-typo-task
-
-Caused by:
-    Task "nonexistent-xyz" not found
+Task "nonexistent-xyz" not found.
+task-select-test#run-typo-task depends on "nonexistent-xyz" via `vt run nonexistent-xyz`.
+Next steps:
+  Run `vt run` to browse available tasks.
+  Check `vite-task.json` and `package.json` scripts where tasks are defined.
diff --git a/crates/vite_task_bin/tests/e2e_snapshots/fixtures/task-select/snapshots/verbose without task errors.snap b/crates/vite_task_bin/tests/e2e_snapshots/fixtures/task-select/snapshots/verbose without task errors.snap
index 3de34734..65f72a8a 100644
--- a/crates/vite_task_bin/tests/e2e_snapshots/fixtures/task-select/snapshots/verbose without task errors.snap	
+++ b/crates/vite_task_bin/tests/e2e_snapshots/fixtures/task-select/snapshots/verbose without task errors.snap	
@@ -5,4 +5,8 @@ info:
   cwd: packages/app
 ---
 [1]> vt run --verbose
-Error: No task specifier provided for 'run' command
+✗ No task specifier provided for 'run' command
+
+Raw details:
+No task specifier provided for 'run' command
+Exit code: 1
diff --git a/crates/vite_task_plan/src/error.rs b/crates/vite_task_plan/src/error.rs
index 66db2783..626d9ffa 100644
--- a/crates/vite_task_plan/src/error.rs
+++ b/crates/vite_task_plan/src/error.rs
@@ -11,6 +11,13 @@ use vite_task_graph::display::TaskDisplay;
 
 use crate::{context::TaskRecursionError, envs::ResolveEnvError};
 
+#[derive(Debug, Clone)]
+pub struct NestedMissingTaskError<'a> {
+    pub parent_task: &'a TaskDisplay,
+    pub command: &'a Str,
+    pub task_name: &'a Str,
+}
+
 #[derive(Debug, thiserror::Error)]
 pub enum CdCommandError {
     #[error("No home directory found for 'cd' command with no arguments")]
@@ -162,3 +169,18 @@ pub enum Error {
     #[error("Cycle dependency detected: {}", _0.iter().map(std::string::ToString::to_string).collect::<Vec<_>>().join(" -> "))]
     CycleDependencyDetected(Vec<TaskDisplay>),
 }
+
+impl Error {
+    #[must_use]
+    pub fn nested_missing_task(&self) -> Option<NestedMissingTaskError<'_>> {
+        match self {
+            Self::NestPlan { task_display, command, error } => match error.as_ref() {
+                Self::NoTasksMatched(task_name) => {
+                    Some(NestedMissingTaskError { parent_task: task_display, command, task_name })
+                }
+                inner => inner.nested_missing_task(),
+            },
+            _ => None,
+        }
+    }
+}