diff --git a/src/docker/mod.rs b/src/docker/mod.rs
index b341736f4..f2c9da22e 100644
--- a/src/docker/mod.rs
+++ b/src/docker/mod.rs
@@ -41,6 +41,7 @@ pub fn run(
             docker_in_docker,
             cwd,
         )
+        .wrap_err("could not complete remote run")
     } else {
         local::run(
             engine,
diff --git a/src/docker/remote.rs b/src/docker/remote.rs
index 2167ed513..5994be4a7 100644
--- a/src/docker/remote.rs
+++ b/src/docker/remote.rs
@@ -4,6 +4,8 @@ use std::path::{Path, PathBuf};
 use std::process::ExitStatus;
 use std::{env, fs, time};
 
+use eyre::Context;
+
 use super::engine::Engine;
 use super::shared::*;
 use crate::cargo::CargoMetadata;
@@ -130,7 +132,7 @@ fn copy_volume_files(
         .arg(src.to_utf8()?)
         .arg(format!("{container}:{}", dst.as_posix()?))
         .run_and_get_status(msg_info, false)
-        .map_err(Into::into)
+        .map(Into::into)
 }
 
 fn is_cachedir_tag(path: &Path) -> Result<bool> {
@@ -221,9 +223,15 @@ pub fn copy_volume_container_cargo(
     } else {
         // can copy a limit subset of files: the rest is present.
         create_volume_dir(engine, container, &dst, msg_info)?;
-        for entry in fs::read_dir(cargo_dir)? {
+        for entry in fs::read_dir(cargo_dir)
+            .wrap_err_with(|| format!("when reading directory {cargo_dir:?}"))?
+        {
             let file = entry?;
-            let basename = file.file_name().to_utf8()?.to_string();
+            let basename = file
+                .file_name()
+                .to_utf8()
+                .wrap_err_with(|| format!("when reading file {file:?}"))?
+                .to_string();
             if !basename.starts_with('.') && !matches!(basename.as_ref(), "git" | "registry") {
                 copy_volume_files(engine, container, &file.path(), &dst, msg_info)?;
             }
@@ -238,7 +246,7 @@ fn copy_dir<Skip>(src: &Path, dst: &Path, depth: u32, skip: Skip) -> Result<()>
 where
     Skip: Copy + Fn(&fs::DirEntry, u32) -> bool,
 {
-    for entry in fs::read_dir(src)? {
+    for entry in fs::read_dir(src).wrap_err_with(|| format!("when reading directory {src:?}"))? {
         let file = entry?;
         if skip(&file, depth) {
             continue;
@@ -247,7 +255,8 @@ where
         let src_path = file.path();
         let dst_path = dst.join(file.file_name());
         if file.file_type()?.is_file() {
-            fs::copy(&src_path, &dst_path)?;
+            fs::copy(&src_path, &dst_path)
+                .wrap_err_with(|| format!("when copying file {src_path:?} -> {dst_path:?}"))?;
         } else {
             fs::create_dir(&dst_path).ok();
             copy_dir(&src_path, &dst_path, depth + 1, skip)?;
@@ -755,7 +764,7 @@ pub(crate) fn run(
 
     // 2. create our volume to copy all our data over to
     if let VolumeId::Discard(ref id) = volume {
-        volume_create(engine, id, msg_info)?;
+        volume_create(engine, id, msg_info).wrap_err("when creating volume")?;
     }
     let _volume_deletter = DeleteVolume(engine, &volume, msg_info);
 
@@ -775,9 +784,11 @@ pub(crate) fn run(
         cwd,
         |_, val| mount_path(val),
         |(src, dst)| volumes.push((src, dst)),
-    )?;
+    )
+    .wrap_err("could not determine mount points")?;
 
-    docker_seccomp(&mut docker, engine.kind, target, metadata)?;
+    docker_seccomp(&mut docker, engine.kind, target, metadata)
+        .wrap_err("when copying seccomp profile")?;
 
     // Prevent `bin` from being mounted inside the Docker container.
     docker.args(&["-v", &format!("{mount_prefix}/cargo/bin")]);
@@ -821,7 +832,8 @@ pub(crate) fn run(
             target,
             mount_prefix_path,
             msg_info,
-        )?;
+        )
+        .wrap_err("when copying xargo")?;
         copy_volume_container_cargo(
             engine,
             &container,
@@ -829,7 +841,8 @@ pub(crate) fn run(
             mount_prefix_path,
             false,
             msg_info,
-        )?;
+        )
+        .wrap_err("when copying cargo")?;
         copy_volume_container_rust(
             engine,
             &container,
@@ -838,7 +851,8 @@ pub(crate) fn run(
             mount_prefix_path,
             false,
             msg_info,
-        )?;
+        )
+        .wrap_err("when copying rust")?;
     } else {
         // need to copy over the target triple if it hasn't been previously copied
         copy_volume_container_rust_triple(
@@ -849,14 +863,16 @@ pub(crate) fn run(
             mount_prefix_path,
             true,
             msg_info,
-        )?;
+        )
+        .wrap_err("when copying rust target files")?;
     }
     let mount_root = if mount_volumes {
         // cannot panic: absolute unix path, must have root
         let rel_mount_root = dirs.mount_root.strip_prefix('/').unwrap();
         let mount_root = mount_prefix_path.join(rel_mount_root);
         if !rel_mount_root.is_empty() {
-            create_volume_dir(engine, &container, mount_root.parent().unwrap(), msg_info)?;
+            create_volume_dir(engine, &container, mount_root.parent().unwrap(), msg_info)
+                .wrap_err("when creating mount root")?;
         }
         mount_root
     } else {
diff --git a/src/lib.rs b/src/lib.rs
index c3db3954d..419db5d02 100644
--- a/src/lib.rs
+++ b/src/lib.rs
@@ -518,7 +518,8 @@ pub fn run() -> Result<ExitStatus> {
                     args.msg_info,
                     args.docker_in_docker,
                     &cwd,
-                )?;
+                )
+                .wrap_err("when running docker")?;
                 let needs_host = args
                     .subcommand
                     .map(|sc| sc.needs_host(is_remote))