diff --git a/src/build.rs b/src/build.rs
index b72e002..b5096eb 100644
--- a/src/build.rs
+++ b/src/build.rs
@@ -46,10 +46,23 @@ pub fn build_source_package(cwd: Option<&Path>) -> Result<(), Box<dyn Error>> {
         );
     }
 
-    let status = command.status()?;
+    let status = command.status().map_err(|e| {
+        format!(
+            "Failed to run 'dpkg-buildpackage': {}. \
+             Is 'dpkg-dev' (which provides dpkg-buildpackage) installed?",
+            e
+        )
+    })?;
 
     if !status.success() {
-        return Err(format!("dpkg-buildpackage failed with status: {}", status).into());
+        return Err(format!(
+            "dpkg-buildpackage failed with status: {}. \
+             Re-run with 'RUST_LOG=debug' for more details, or run \
+             'dpkg-buildpackage -S -I -i -nc -d' manually in '{}' to see the full output.",
+            status,
+            cwd.display()
+        )
+        .into());
     }
 
     if signing_key.is_some() {
diff --git a/src/changelog.rs b/src/changelog.rs
index 06270cc..4cc42e9 100644
--- a/src/changelog.rs
+++ b/src/changelog.rs
@@ -119,10 +119,24 @@ fn increment_suffix(version: &str, suffix: &str) -> String {
 pub fn parse_changelog_header(
     path: &Path,
 ) -> Result<(String, String, String), Box<dyn std::error::Error>> {
-    let file = File::open(path)?;
+    let file = File::open(path).map_err(|e| {
+        format!(
+            "Failed to read changelog '{}': {}. \
+             Make sure you are running this command from the root of a source package \
+             (a directory containing a 'debian/' subdirectory with a 'changelog' file).",
+            path.display(),
+            e
+        )
+    })?;
     let mut reader = io::BufReader::new(file);
     let mut first_line = String::new();
-    reader.read_line(&mut first_line)?;
+    reader.read_line(&mut first_line).map_err(|e| {
+        format!(
+            "Failed to read first line of changelog '{}': {}",
+            path.display(),
+            e
+        )
+    })?;
 
     // Format: package (version) series; urgency=urgency
     let re = Regex::new(r"^(\S+) \(([^)]+)\) (.*); .*")?;
@@ -132,16 +146,37 @@ pub fn parse_changelog_header(
         let series = caps.get(3).map_or("", |m| m.as_str()).to_string();
         Ok((package, version, series))
     } else {
-        Err(format!("Invalid changelog header format in {}", path.display()).into())
+        Err(format!(
+            "Invalid changelog header format in '{}'. \
+             The first line must look like: `package (version) series; urgency=...`, \
+             but got: {:?}",
+            path.display(),
+            first_line.trim_end()
+        )
+        .into())
     }
 }
 
 /// Parse a changelog file footer to extract maintainer information
 /// Returns (name, email) tuple from the last modification entry
 pub fn parse_changelog_footer(path: &Path) -> Result<(String, String), Box<dyn std::error::Error>> {
-    let mut file = File::open(path)?;
+    let mut file = File::open(path).map_err(|e| {
+        format!(
+            "Failed to read changelog '{}': {}. \
+             Make sure you are running this command from the root of a source package \
+             (a directory containing a 'debian/' subdirectory with a 'changelog' file).",
+            path.display(),
+            e
+        )
+    })?;
     let mut content = String::new();
-    file.read_to_string(&mut content)?;
+    file.read_to_string(&mut content).map_err(|e| {
+        format!(
+            "Failed to read changelog '{}': {}",
+            path.display(),
+            e
+        )
+    })?;
 
     // Find the last maintainer line (format: -- Name <email>  Date)
     let re = Regex::new(r"--\s*([^<]+?)\s*<([^>]+)>\s*")?;
@@ -159,7 +194,13 @@ pub fn parse_changelog_footer(path: &Path) -> Result<(String, String), Box<dyn s
             .to_string();
         Ok((name, email))
     } else {
-        Err(format!("No maintainer information found in {}", path.display()).into())
+        Err(format!(
+            "No maintainer information found in '{}'. \
+             The changelog must contain a line of the form '-- Name <email>  Date', \
+             but none was found.",
+            path.display()
+        )
+        .into())
     }
 }
 
@@ -283,9 +324,31 @@ fn get_maintainer_info() -> Result<(String, String), Box<dyn std::error::Error>>
     }
 
     // From git config
-    let config = git2::Config::open_default()?;
-    let name = config.get_string("user.name")?;
-    let email = config.get_string("user.email")?;
+    let config = git2::Config::open_default().map_err(|e| {
+        format!(
+            "Could not determine maintainer information. \
+             Neither $DEBFULLNAME/$DEBEMAIL nor git configuration is available: {}. \
+             Set the DEBFULLNAME and DEBEMAIL environment variables, \
+             or configure git with `git config --global user.name` and `git config --global user.email`.",
+            e
+        )
+    })?;
+    let name = config.get_string("user.name").map_err(|e| {
+        format!(
+            "Could not find git 'user.name' configuration: {}. \
+             Set it with `git config --global user.name \"Your Name\"` \
+             or define the DEBFULLNAME environment variable.",
+            e
+        )
+    })?;
+    let email = config.get_string("user.email").map_err(|e| {
+        format!(
+            "Could not find git 'user.email' configuration: {}. \
+             Set it with `git config --global user.email \"you@example.com\"` \
+             or define the DEBEMAIL environment variable.",
+            e
+        )
+    })?;
     Ok((name, email))
 }
 
diff --git a/src/context/api.rs b/src/context/api.rs
index 7ee38b3..71d41b1 100644
--- a/src/context/api.rs
+++ b/src/context/api.rs
@@ -292,21 +292,43 @@ impl<'a> ContextCommand<'a> {
 
     /// Run command and obtain exit status
     pub fn status(&mut self) -> io::Result<std::process::ExitStatus> {
-        self.context.driver().as_ref().unwrap().run(
-            &self.program,
-            &self.args,
-            &self.env,
-            self.cwd.as_deref(),
-        )
+        let program = self.program.clone();
+        self.context
+            .driver()
+            .as_ref()
+            .unwrap()
+            .run(&self.program, &self.args, &self.env, self.cwd.as_deref())
+            .map_err(|e| contextualize_spawn_error(&program, e))
     }
 
     /// Run command, capturing output
     pub fn output(&mut self) -> io::Result<std::process::Output> {
-        self.context.driver().as_ref().unwrap().run_output(
-            &self.program,
-            &self.args,
-            &self.env,
-            self.cwd.as_deref(),
-        )
+        let program = self.program.clone();
+        self.context
+            .driver()
+            .as_ref()
+            .unwrap()
+            .run_output(&self.program, &self.args, &self.env, self.cwd.as_deref())
+            .map_err(|e| contextualize_spawn_error(&program, e))
+    }
+}
+
+/// Wrap an I/O error from launching a command with a more helpful message.
+///
+/// In particular, a `NotFound` error (e.g. "No such file or directory") is almost always
+/// caused by the requested program not being installed or not on `PATH`; we make that
+/// explicit instead of leaking the raw OS error.
+fn contextualize_spawn_error(program: &str, e: io::Error) -> io::Error {
+    if e.kind() == io::ErrorKind::NotFound {
+        io::Error::new(
+            e.kind(),
+            format!(
+                "Could not run '{program}': {e}. \
+                 The program does not seem to be installed or is not on PATH; \
+                 install the corresponding package and retry.",
+            ),
+        )
+    } else {
+        io::Error::new(e.kind(), format!("Could not run '{program}': {e}"))
     }
 }
diff --git a/src/context/local.rs b/src/context/local.rs
index b20f008..d115e16 100644
--- a/src/context/local.rs
+++ b/src/context/local.rs
@@ -2,6 +2,7 @@
 /// Context driver: Does nothing
 use super::api::ContextDriver;
 use std::io;
+use std::os::unix::fs::symlink;
 use std::path::{Path, PathBuf};
 use std::process::Command;
 use std::time::SystemTime;
@@ -112,6 +113,14 @@ impl ContextDriver for LocalDriver {
 }
 
 fn copy_dir_recursive(src: &Path, dest: &Path) -> io::Result<()> {
+    // Reproduce symlinks as symlinks rather than following them, so that
+    // dangling/absolute symlinks do not abort the copy.
+    if std::fs::symlink_metadata(src)?.file_type().is_symlink() {
+        let target = std::fs::read_link(src)?;
+        let _ = std::fs::remove_file(dest);
+        return symlink(&target, dest);
+    }
+
     if src.is_dir() {
         std::fs::create_dir_all(dest)?;
         for entry in std::fs::read_dir(src)? {
diff --git a/src/context/mod.rs b/src/context/mod.rs
index 5800197..cd1c412 100644
--- a/src/context/mod.rs
+++ b/src/context/mod.rs
@@ -147,4 +147,37 @@ mod tests {
             "subcontent"
         );
     }
+
+    /// Copying a tree containing a dangling symlink must reproduce the link
+    /// itself rather than failing to follow it (which previously surfaced as
+    /// a bare "No such file or directory (os error 2)").
+    #[test]
+    fn test_context_copy_preserves_dangling_symlink() {
+        use std::os::unix::fs::symlink;
+        let temp_dir = tempfile::tempdir().unwrap();
+        let ctx = Context::new(ContextConfig::Local);
+
+        let src_dir = temp_dir.path().join("src");
+        std::fs::create_dir_all(&src_dir).unwrap();
+        // A regular file alongside the symlink, to ensure normal copies still work.
+        std::fs::write(src_dir.join("real.txt"), "data").unwrap();
+        // A dangling symlink pointing to a non-existent target.
+        symlink("/nonexistent/target", src_dir.join("dangling")).unwrap();
+
+        let dest_dir = temp_dir.path().join("dest");
+        ctx.copy_path(&src_dir, &dest_dir).unwrap();
+
+        // The regular file was copied.
+        assert_eq!(
+            ctx.read_file(&dest_dir.join("real.txt")).unwrap(),
+            "data"
+        );
+        // The symlink was reproduced as a symlink (not followed).
+        let meta = std::fs::symlink_metadata(dest_dir.join("dangling")).unwrap();
+        assert!(meta.file_type().is_symlink());
+        assert_eq!(
+            std::fs::read_link(dest_dir.join("dangling")).unwrap(),
+            std::path::Path::new("/nonexistent/target")
+        );
+    }
 }
diff --git a/src/context/unshare.rs b/src/context/unshare.rs
index 89ac3de..bc6f2b0 100644
--- a/src/context/unshare.rs
+++ b/src/context/unshare.rs
@@ -1,6 +1,8 @@
 use super::api::{Context, ContextCommand, ContextDriver};
 use log::debug;
+use std::fs;
 use std::io;
+use std::os::unix::fs::symlink;
 use std::path::{Path, PathBuf};
 use std::sync::Arc;
 
@@ -9,23 +11,88 @@ pub struct UnshareDriver {
     pub parent: Option<Arc<super::api::Context>>,
 }
 
-/// Recursively copy a directory and all its contents
+/// Recursively copy a directory and all its contents.
+///
+/// Symlinks are copied as symlinks (preserving the link target rather than
+/// following it), so that dangling links do not abort the copy.
 fn copy_dir_recursive(src: &Path, dest: &Path) -> io::Result<()> {
     // Create the destination directory
-    std::fs::create_dir_all(dest)?;
+    std::fs::create_dir_all(dest).map_err(|e| {
+        io::Error::new(
+            e.kind(),
+            format!("Failed to create directory '{}': {}", dest.display(), e),
+        )
+    })?;
 
     // Iterate through the source directory
-    for entry in std::fs::read_dir(src)? {
-        let entry = entry?;
+    let read = std::fs::read_dir(src).map_err(|e| {
+        io::Error::new(
+            e.kind(),
+            format!("Failed to read directory '{}': {}", src.display(), e),
+        )
+    })?;
+    for entry in read {
+        let entry = entry.map_err(|e| {
+            io::Error::new(
+                e.kind(),
+                format!("Failed to read entry in '{}': {}", src.display(), e),
+            )
+        })?;
         let src_path = entry.path();
         let dest_path = dest.join(entry.file_name());
 
-        if src_path.is_dir() {
+        // Handle symlinks explicitly: reproduce the link itself instead of
+        // following it. This avoids failing on dangling/absolute symlinks.
+        let metadata = match std::fs::symlink_metadata(&src_path) {
+            Ok(m) => m,
+            Err(e) => {
+                return Err(io::Error::new(
+                    e.kind(),
+                    format!(
+                        "Failed to read metadata of '{}': {}",
+                        src_path.display(),
+                        e
+                    ),
+                ))
+            }
+        };
+
+        if metadata.file_type().is_symlink() {
+            let target = std::fs::read_link(&src_path).map_err(|e| {
+                io::Error::new(
+                    e.kind(),
+                    format!("Failed to read symlink '{}': {}", src_path.display(), e),
+                )
+            })?;
+            // Remove an existing destination entry (e.g. from a previous attempt)
+            let _ = fs::remove_file(&dest_path);
+            symlink(&target, &dest_path).map_err(|e| {
+                io::Error::new(
+                    e.kind(),
+                    format!(
+                        "Failed to create symlink '{}' -> '{}': {}",
+                        dest_path.display(),
+                        target.display(),
+                        e
+                    ),
+                )
+            })?;
+        } else if src_path.is_dir() {
             // Recursively copy subdirectories
             copy_dir_recursive(&src_path, &dest_path)?;
         } else {
-            // Copy files
-            std::fs::copy(&src_path, &dest_path)?;
+            // Copy regular files
+            std::fs::copy(&src_path, &dest_path).map_err(|e| {
+                io::Error::new(
+                    e.kind(),
+                    format!(
+                        "Failed to copy '{}' to '{}': {}",
+                        src_path.display(),
+                        dest_path.display(),
+                        e
+                    ),
+                )
+            })?;
         }
     }
 
diff --git a/src/deb/local.rs b/src/deb/local.rs
index b44dccb..6270a10 100644
--- a/src/deb/local.rs
+++ b/src/deb/local.rs
@@ -138,10 +138,20 @@ pub async fn build(
         .command("apt-get")
         .envs(env.clone())
         .arg("update")
-        .status()?;
+        .status()
+        .map_err(|e| {
+            format!(
+                "Failed to run 'apt-get update' inside the build context: {}. \
+                 If this is a local build, make sure apt-get is available and \
+                 try executing with sudo.",
+                e
+            )
+        })?;
     if !status.success() {
         return Err(
-            "Could not execute apt-get update. If this is a local build, try executing with sudo."
+            "apt-get update failed inside the build context. \
+             If this is a local build, try executing with sudo, \
+             or re-run with RUST_LOG=debug for more details."
                 .into(),
         );
     }
diff --git a/src/distro_info.rs b/src/distro_info.rs
index d2ea4d5..cbb9d32 100644
--- a/src/distro_info.rs
+++ b/src/distro_info.rs
@@ -110,11 +110,30 @@ fn parse_series_csv(content: &str) -> Result<Vec<SeriesInformation>, Box<dyn Err
     Ok(series_info_list)
 }
 
+/// List the distributions known to pkh (e.g. "debian", "ubuntu")
+pub fn supported_dists() -> Vec<String> {
+    DATA.dist.keys().cloned().collect()
+}
+
 /// Get time-ordered list of series information for a distribution, development series first
 pub async fn get_ordered_series(dist: &str) -> Result<Vec<SeriesInformation>, Box<dyn Error>> {
-    let series_info = &DATA.dist.get(dist).unwrap().series;
+    let dist_data = DATA.dist.get(dist).ok_or_else(|| {
+        format!(
+            "Unknown distribution '{}'. Supported distributions are: {}.",
+            dist,
+            supported_dists().join(", ")
+        )
+    })?;
+    let series_info = &dist_data.series;
     let content = if Path::new(series_info.local.as_str()).exists() {
-        std::fs::read_to_string(format!("/usr/share/distro-info/{dist}.csv"))?
+        std::fs::read_to_string(format!("/usr/share/distro-info/{dist}.csv"))
+            .map_err(|e| {
+                format!(
+                    "Failed to read distribution series data for '{dist}' \
+                     from '{}': {}. The 'distro-info' package provides these CSV files.",
+                    series_info.local, e
+                )
+            })?
     } else {
         reqwest::get(series_info.network.as_str())
             .await?
@@ -188,13 +207,20 @@ pub async fn get_dist_from_series(series: &str) -> Result<String, Box<dyn Error>
 /// Get the package pockets available for a given distribution
 ///
 /// Example: get_dist_pockets(ubuntu) => ["proposed", "updates", ""]
-pub fn get_dist_pockets(dist: &str) -> Vec<String> {
-    let mut pockets = DATA.dist.get(dist).unwrap().pockets.clone();
+pub fn get_dist_pockets(dist: &str) -> Result<Vec<String>, Box<dyn Error>> {
+    let dist_data = DATA.dist.get(dist).ok_or_else(|| {
+        format!(
+            "Unknown distribution '{}'. Supported distributions are: {}.",
+            dist,
+            supported_dists().join(", ")
+        )
+    })?;
+    let mut pockets = dist_data.pockets.clone();
 
     // Explicitely add 'main' pocket, which is just the empty string
     pockets.push("".to_string());
 
-    pockets
+    Ok(pockets)
 }
 
 /// Get the sources URL for a distribution, series, pocket, and component
@@ -210,8 +236,17 @@ pub fn get_sources_url(base_url: &str, series: &str, pocket: &str, component: &s
 /// Get the archive base URL for a distribution
 ///
 /// Example: ubuntu => http://archive.ubuntu.com/ubuntu
-pub fn get_base_url(dist: &str) -> String {
-    DATA.dist.get(dist).unwrap().base_url.clone()
+pub fn get_base_url(dist: &str) -> Result<String, Box<dyn Error>> {
+    DATA.dist.get(dist)
+        .map(|d| d.base_url.clone())
+        .ok_or_else(|| {
+            format!(
+                "Unknown distribution '{}'. Supported distributions are: {}.",
+                dist,
+                supported_dists().join(", ")
+            )
+            .into()
+        })
 }
 
 /// Obtain the URLs for the archive keyrings of a distribution series
@@ -246,7 +281,15 @@ pub async fn get_keyring_urls(series: &str) -> Result<Vec<String>, Box<dyn Error
                 Ok(urls)
             }
         } else {
-            let series_num = get_debian_series_number(series).await?.unwrap();
+            let series_num = get_debian_series_number(series)
+                .await?
+                .ok_or_else(|| {
+                    format!(
+                        "Could not determine the version number for Debian series '{series}'. \
+                         Make sure the 'distro-info' package is installed, which provides the \
+                         series CSV data used to map series names to version numbers."
+                    )
+                })?;
             // Replace {series_num} placeholder with the actual series number
             Ok(vec![
                 dist_data
@@ -297,9 +340,23 @@ pub async fn get_components(
 
 /// Map a Debian series name to its version number
 pub async fn get_debian_series_number(series: &str) -> Result<Option<String>, Box<dyn Error>> {
-    let series_info = &DATA.dist.get("debian").unwrap().series;
+    let dist_data = DATA.dist.get("debian").ok_or_else(|| {
+        format!(
+            "Debian distribution data is missing from the built-in configuration. \
+             This is a bug; supported distributions are: {}.",
+            supported_dists().join(", ")
+        )
+    })?;
+    let series_info = &dist_data.series;
     let content = if Path::new(series_info.local.as_str()).exists() {
-        std::fs::read_to_string(series_info.local.as_str())?
+        std::fs::read_to_string(series_info.local.as_str())
+            .map_err(|e| {
+                format!(
+                    "Failed to read Debian series data from '{}': {}. \
+                     The 'distro-info' package provides this file.",
+                    series_info.local, e
+                )
+            })?
     } else {
         reqwest::get(series_info.network.as_str())
             .await?
diff --git a/src/main.rs b/src/main.rs
index 7dbb07d..910a518 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -14,6 +14,17 @@ use log::{error, info};
 
 mod ui;
 
+/// Obtain the current working directory, exiting with a helpful message on failure.
+fn current_dir_or_exit() -> std::path::PathBuf {
+    match std::env::current_dir() {
+        Ok(p) => p,
+        Err(e) => {
+            error!("Could not determine the current working directory: {}", e);
+            std::process::exit(1);
+        }
+    }
+}
+
 fn main() {
     let rt = tokio::runtime::Runtime::new().unwrap();
     let logger =
@@ -137,7 +148,7 @@ fn main() {
             info!("Done.");
         }
         Some(("chlog", sub_matches)) => {
-            let cwd = std::env::current_dir().unwrap();
+            let cwd = current_dir_or_exit();
             let version = sub_matches.get_one::<String>("version").map(|s| s.as_str());
 
             if let Err(e) = generate_entry("debian/changelog", Some(&cwd), version) {
@@ -145,21 +156,38 @@ fn main() {
                 std::process::exit(1);
             }
 
-            let editor = std::env::var("EDITOR").unwrap();
-            let _status = std::process::Command::new(editor)
+            let editor = match std::env::var("EDITOR") {
+                Ok(e) => e,
+                Err(_) => {
+                    error!(
+                        "No editor configured. Set the EDITOR environment variable \
+                         (e.g. `EDITOR=nano` or `export EDITOR=vim`) and retry."
+                    );
+                    std::process::exit(1);
+                }
+            };
+            let _status = std::process::Command::new(&editor)
                 .current_dir(&cwd)
                 .args(["debian/changelog"])
-                .status();
+                .status()
+                .map_err(|e| {
+                    error!(
+                        "Could not launch editor '{}': {}. \
+                         Make sure it is installed and available on PATH.",
+                        editor, e
+                    );
+                    std::process::exit(1);
+                });
         }
         Some(("build", _sub_matches)) => {
-            let cwd = std::env::current_dir().unwrap();
+            let cwd = current_dir_or_exit();
             if let Err(e) = pkh::build::build_source_package(Some(&cwd)) {
                 error!("{}", e);
                 std::process::exit(1);
             }
         }
         Some(("deb", sub_matches)) => {
-            let cwd = std::env::current_dir().unwrap();
+            let cwd = current_dir_or_exit();
             let series = sub_matches.get_one::<String>("series").map(|s| s.as_str());
             let arch = sub_matches.get_one::<String>("arch").map(|s| s.as_str());
             let cross = sub_matches.get_one::<bool>("cross").unwrap_or(&false);
@@ -221,7 +249,13 @@ fn main() {
                         "ssh" => {
                             let endpoint = args
                                 .get_one::<String>("endpoint")
-                                .expect("Endpoint is required for ssh context");
+                                .unwrap_or_else(|| {
+                                    error!(
+                                        "An --endpoint is required to create an ssh context. \
+                                         Expected format: [ssh://][user@]host[:port]"
+                                    );
+                                    std::process::exit(1);
+                                });
 
                             // Parse host, user, port from endpoint
                             // Formats: [ssh://][user@]host[:port]
diff --git a/src/package_info.rs b/src/package_info.rs
index 2c4438a..fbcf584 100644
--- a/src/package_info.rs
+++ b/src/package_info.rs
@@ -213,7 +213,7 @@ async fn get(
     }
 
     // Determine the base URL to use (either provided PPA URL or default archive)
-    let distro_base_url = crate::distro_info::get_base_url(&dist);
+    let distro_base_url = crate::distro_info::get_base_url(&dist)?;
     let base_url = if let Some(ppa_url) = base_url {
         ppa_url.to_string()
     } else {
@@ -298,7 +298,7 @@ async fn find_package(
         }
 
         let pockets = if pocket.is_empty() {
-            crate::distro_info::get_dist_pockets(dist)
+            crate::distro_info::get_dist_pockets(dist)?
         } else {
             vec![pocket.to_string()]
         };
diff --git a/src/pull.rs b/src/pull.rs
index 19df76e..c715583 100644
--- a/src/pull.rs
+++ b/src/pull.rs
@@ -1,5 +1,6 @@
 use std::cmp::min;
 use std::error::Error;
+use std::os::unix::fs::symlink;
 use std::path::Path;
 use std::path::PathBuf;
 
@@ -101,7 +102,13 @@ fn copy_dir_all(src: &Path, dst: &Path) -> Result<(), Box<dyn Error>> {
         let src_path = entry.path();
         let dst_path = dst.join(entry.file_name());
 
-        if src_path.is_dir() {
+        // Reproduce symlinks as symlinks rather than following them, so that
+        // dangling/absolute symlinks do not abort the copy.
+        if std::fs::symlink_metadata(&src_path)?.file_type().is_symlink() {
+            let target = std::fs::read_link(&src_path)?;
+            let _ = std::fs::remove_file(&dst_path);
+            symlink(&target, &dst_path)?;
+        } else if src_path.is_dir() {
             copy_dir_all(&src_path, &dst_path)?;
         } else {
             std::fs::copy(&src_path, &dst_path)?;
@@ -183,12 +190,25 @@ fn checkout_pristine_tar(package_dir: &Path, filename: &str) -> Result<(), Box<d
         .current_dir(package_dir)
         .args(["checkout", format!("../{filename}").as_str()])
         .output()
-        .expect("pristine-tar checkout failed");
+        .map_err(|e| {
+            format!(
+                "Failed to run 'pristine-tar' to check out '{filename}': {}. \
+                 Is 'pristine-tar' installed? It is required to reconstruct \
+                 the upstream orig tarball from a git repository.",
+                e
+            )
+        })?;
 
     if !output.status.success() {
+        let stderr = String::from_utf8_lossy(&output.stderr);
         return Err(format!(
-            "pristine-tar checkout failed with status: {}",
-            output.status
+            "pristine-tar checkout of '{filename}' failed with status: {}.{}",
+            output.status,
+            if stderr.trim().is_empty() {
+                String::new()
+            } else {
+                format!("\npristine-tar output:\n{}", stderr.trim())
+            }
         )
         .into());
     }