diff --git a/manifest/src/lib.rs b/manifest/src/lib.rs
index 014c68be9..3c4c4ce4d 100644
--- a/manifest/src/lib.rs
+++ b/manifest/src/lib.rs
@@ -42,7 +42,8 @@ pub fn get_manifests<P: AsRef<Path>>(path: P) -> Result<Vec<Manifest>> {
 }
 
 fn parse_cargo_manifest(path: &Path) -> Result<Manifest> {
-    let m = cargo_toml::Manifest::from_path(path)?;
+    let m = cargo_toml::Manifest::from_path(path)
+        .with_context(|| format!("Failed to parse Cargo.toml at '{}'", path.display()))?;
     let package = m.package.context("Not a package (only a workspace)")?;
     let description = package.description().map(|v| v.into());
 
@@ -57,7 +58,8 @@ fn parse_cargo_manifest(path: &Path) -> Result<Manifest> {
 }
 
 fn parse_npm_manifest(path: &Path) -> Result<Manifest> {
-    let package = npm_package_json::Package::from_path(path)?;
+    let package = npm_package_json::Package::from_path(path)
+        .with_context(|| format!("Failed to parse package.json at '{}'", path.display()))?;
     Ok(Manifest {
         manifest_type: ManifestType::Npm,
         number_of_dependencies: package.dependencies.len(),
diff --git a/src/info/git/mod.rs b/src/info/git/mod.rs
index 8c2065513..210240052 100644
--- a/src/info/git/mod.rs
+++ b/src/info/git/mod.rs
@@ -222,7 +222,7 @@ fn should_break(
         return false;
     }
 
-    max_churn_pool_size_opt.map_or(true, |max_churn_pool_size| {
+    max_churn_pool_size_opt.is_none_or(|max_churn_pool_size| {
         number_of_diffs_computed >= max_churn_pool_size.min(total_number_of_commits)
     })
 }
diff --git a/src/info/langs/mod.rs b/src/info/langs/mod.rs
index f723d9921..f4b5a2e3f 100644
--- a/src/info/langs/mod.rs
+++ b/src/info/langs/mod.rs
@@ -21,8 +21,14 @@ pub fn get_loc_by_language_sorted(
 ) -> Result<Vec<(Language, usize)>> {
     let locs = get_locs(dir, globs_to_exclude, language_types, include_hidden);
 
-    let loc_by_language =
-        get_loc_by_language(&locs).context("Could not find any source code in this repository")?;
+    let loc_by_language = get_loc_by_language(&locs).with_context(|| {
+        format!(
+            "No source code found in the repository at '{}'. \
+         Note: Some language types (prose, data) are excluded by default. \
+         Consider using the '--type' option to include them.",
+            dir.display()
+        )
+    })?;
 
     let loc_by_language_sorted = sort_by_loc(loc_by_language);
 
diff --git a/src/info/license.rs b/src/info/license.rs
index 20b74d663..2713fa85c 100644
--- a/src/info/license.rs
+++ b/src/info/license.rs
@@ -22,8 +22,8 @@ impl Detector {
     pub fn new() -> Result<Self> {
         match Store::from_cache(CACHE_DATA) {
             Ok(store) => Ok(Self { store }),
-            Err(_) => {
-                bail!("Could not initialize the license detector")
+            Err(e) => {
+                bail!("Could not initialize the license detector: {}", e)
             }
         }
     }
diff --git a/src/info/mod.rs b/src/info/mod.rs
index a5c2a54ec..933f0857d 100644
--- a/src/info/mod.rs
+++ b/src/info/mod.rs
@@ -147,14 +147,16 @@ pub fn build_info(cli_options: &CliOptions) -> Result<Info> {
         &repo,
         cli_options.info.hide_token,
         cli_options.info.http_url,
-    )?;
+    )
+    .context("Failed to determine repository URL")?;
 
     let git_metrics = traverse_commit_graph(
         &repo,
         cli_options.info.no_bots.clone(),
         cli_options.info.churn_pool_size,
         cli_options.info.no_merges,
-    )?;
+    )
+    .context("Failed to traverse Git commit history")?;
     let true_color = match cli_options.ascii.true_color {
         When::Always => true,
         When::Never => false,
diff --git a/src/ui/printer.rs b/src/ui/printer.rs
index 6661dbeb8..a5f07b5a0 100644
--- a/src/ui/printer.rs
+++ b/src/ui/printer.rs
@@ -31,10 +31,13 @@ pub struct Printer<W> {
 
 impl<W: Write> Printer<W> {
     pub fn new(writer: W, info: Info, cli_options: CliOptions) -> Result<Self> {
-        let image = match cli_options.image.image {
-            Some(p) => Some(image::open(p).context("Could not load the specified image")?),
-            None => None,
-        };
+        let image =
+            match cli_options.image.image {
+                Some(p) => Some(image::open(&p).with_context(|| {
+                    format!("Could not load the image file at '{}'", p.display())
+                })?),
+                None => None,
+            };
 
         let image_backend = if image.is_some() {
             cli_options
@@ -83,7 +86,7 @@ impl<W: Write> Printer<W> {
                     let image_backend = self
                         .image_backend
                         .as_ref()
-                        .context("Could not detect a supported image backend")?;
+                        .context("No supported image backend detected on your system")?;
 
                     buf.push_str(
                         &image_backend
@@ -92,7 +95,7 @@ impl<W: Write> Printer<W> {
                                 custom_image,
                                 self.color_resolution,
                             )
-                            .context("Error while drawing image")?,
+                            .context("Failed to render the image in the terminal")?,
                     );
                 } else {
                     let mut logo_lines = if let Some(custom_ascii) = &self.ascii_input {