diff --git a/Cargo.lock b/Cargo.lock
index bab43c0433df..2bb8fda8fbfc 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -4475,6 +4475,7 @@ dependencies = [
  "rustc-hash 2.0.0",
  "serde",
  "serde_json",
+ "tempfile",
  "textwrap",
  "thiserror",
  "tikv-jemallocator",
@@ -4506,6 +4507,7 @@ dependencies = [
  "uv-types",
  "uv-virtualenv",
  "uv-warnings",
+ "which",
 ]
 
 [[package]]
diff --git a/crates/uv/Cargo.toml b/crates/uv/Cargo.toml
index 19bfbffe4ea6..67f7a50a2ce7 100644
--- a/crates/uv/Cargo.toml
+++ b/crates/uv/Cargo.toml
@@ -59,6 +59,7 @@ regex = { workspace = true }
 rustc-hash = { workspace = true }
 serde = { workspace = true }
 serde_json = { workspace = true }
+tempfile = { workspace = true }
 textwrap = { workspace = true }
 thiserror = { workspace = true }
 tokio = { workspace = true }
@@ -69,6 +70,7 @@ tracing-subscriber = { workspace = true, features = ["json"] }
 tracing-tree = { workspace = true }
 unicode-width = { workspace = true }
 url = { workspace = true }
+which = { workspace = true }
 
 [target.'cfg(target_os = "windows")'.dependencies]
 mimalloc = { version = "0.1.39" }
diff --git a/crates/uv/src/commands/help.rs b/crates/uv/src/commands/help.rs
index aa83f8a822a2..3f79b3c0884d 100644
--- a/crates/uv/src/commands/help.rs
+++ b/crates/uv/src/commands/help.rs
@@ -1,8 +1,10 @@
-use std::fmt::Write;
+use std::{fmt::Display, fmt::Write};
 
+use anstream::ColorChoice;
 use anyhow::{anyhow, Result};
 use clap::CommandFactory;
-use itertools::Itertools;
+use itertools::{Either, Itertools};
+use which::which;
 
 use super::ExitStatus;
 use crate::printer::Printer;
@@ -30,7 +32,24 @@ pub(crate) fn help(query: &[String], printer: Printer) -> Result<ExitStatus> {
 
     let mut command = command.clone();
     let help = command.render_long_help();
-    writeln!(printer.stderr(), "{}", help.ansi())?;
+
+    let help_ansi = match anstream::Stderr::choice(&std::io::stderr()) {
+        ColorChoice::Always | ColorChoice::AlwaysAnsi => Either::Left(help.ansi()),
+        ColorChoice::Never => Either::Right(help.clone()),
+        // We just asked anstream for a choice, that can't be auto
+        ColorChoice::Auto => unreachable!(),
+    };
+
+    if which("less").is_ok() {
+        // When using less, we use the command name as the file name and can support colors
+        let prompt = format!("help: uv {}", query.join(" "));
+        write_and_spawn(&query.join("-"), &help_ansi, "less", &["-R", "-P", &prompt])?;
+    } else if which("more").is_ok() {
+        // When using more, we skip the ANSI color codes
+        write_and_spawn(&query.join("-"), &help, "more", &[])?;
+    } else {
+        writeln!(printer.stderr(), "{help_ansi}")?;
+    }
 
     Ok(ExitStatus::Success)
 }
@@ -49,3 +68,30 @@ fn find_command<'a>(
     let subcommand = cmd.find_subcommand(next).ok_or((query, cmd))?;
     find_command(&query[1..], subcommand)
 }
+
+/// Write the contents of documentation to disk and spawn the given command to
+/// display it.
+fn write_and_spawn(name: &str, contents: impl Display, command: &str, args: &[&str]) -> Result<()> {
+    // Note this implementation is based on Cargo's `help` command which displays a `man` page.
+    // See https://github.com/rust-lang/cargo/blob/e98f702d83d3075b2232b4502114f177826fe06d/src/bin/cargo/commands/help.rs
+    use std::io::Write;
+
+    let prefix = format!("uv-{name}.");
+    let mut tmp = tempfile::Builder::new().prefix(&prefix).tempfile()?;
+    let f = tmp.as_file_mut();
+    write!(f, "{contents}")?;
+    f.flush()?;
+
+    let path = tmp.path();
+    // Use a path relative to the temp directory so that it can work on
+    // cygwin/msys systems which don't handle windows-style paths.
+    let mut relative_name = std::ffi::OsString::from("./");
+    relative_name.push(path.file_name().unwrap());
+    let mut cmd = std::process::Command::new(command)
+        .args(args)
+        .arg(relative_name)
+        .current_dir(path.parent().unwrap())
+        .spawn()?;
+    drop(cmd.wait());
+    Ok(())
+}
diff --git a/crates/uv/tests/help.rs b/crates/uv/tests/help.rs
index b8d8f26c48f3..f521a2ab4bd9 100644
--- a/crates/uv/tests/help.rs
+++ b/crates/uv/tests/help.rs
@@ -11,8 +11,6 @@ fn help() {
     success: true
     exit_code: 0
     ----- stdout -----
-
-    ----- stderr -----
     An extremely fast Python package manager.
 
     Usage: uv [OPTIONS] <COMMAND>
@@ -109,6 +107,7 @@ fn help() {
       -V, --version
               Print version
 
+    ----- stderr -----
     "###);
 }
 
@@ -230,8 +229,6 @@ fn help_subcommand() {
     success: true
     exit_code: 0
     ----- stdout -----
-
-    ----- stderr -----
     Manage Python installations
 
     Usage: python <COMMAND>
@@ -248,6 +245,7 @@ fn help_subcommand() {
       -h, --help
               Print help (see a summary with '-h')
 
+    ----- stderr -----
     "###);
 }
 
@@ -259,8 +257,6 @@ fn help_subsubcommand() {
     success: true
     exit_code: 0
     ----- stdout -----
-
-    ----- stderr -----
     Download and install Python versions
 
     Usage: install [OPTIONS] [TARGETS]...
@@ -280,6 +276,7 @@ fn help_subsubcommand() {
       -h, --help
               Print help (see a summary with '-h')
 
+    ----- stderr -----
     "###);
 }
 
@@ -449,8 +446,6 @@ fn help_with_global_option() {
     success: true
     exit_code: 0
     ----- stdout -----
-
-    ----- stderr -----
     An extremely fast Python package manager.
 
     Usage: uv [OPTIONS] <COMMAND>
@@ -547,6 +542,7 @@ fn help_with_global_option() {
       -V, --version
               Print version
 
+    ----- stderr -----
     "###);
 }