diff --git a/src/main.rs b/src/main.rs
index 9fe46c1..61a60d6 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -1,10 +1,10 @@
-use anyhow::{Context, Result, bail};
+use anyhow::{Context, Result, anyhow, bail};
 use base64::Engine;
 use clap::{Args, CommandFactory, Parser, Subcommand, ValueEnum};
 use std::collections::{BTreeMap, HashMap};
 use std::ffi::OsStr;
 use std::fs;
-use std::io::Write;
+use std::io::{ErrorKind, Write};
 #[cfg(unix)]
 use std::os::unix::fs::{PermissionsExt, symlink};
 use std::path::{Path, PathBuf};
@@ -2105,16 +2105,8 @@ fn run_target_command(
         cmd.env(k, v);
     }
 
-    let output = cmd.output().with_context(|| {
-        if is_root_fs(root) {
-            format!("failed to execute `{}`", resolved_program_display)
-        } else {
-            format!(
-                "failed to execute `chroot {} {}`",
-                root.display(),
-                resolved_program_display
-            )
-        }
+    let output = cmd.output().map_err(|err| {
+        command_spawn_error(root, &resolved_program, &resolved_program_display, err)
     })?;
 
     if output.status.success() {
@@ -2153,6 +2145,199 @@ fn run_target_command(
     );
 }
 
+fn command_spawn_error(
+    root: &Path,
+    resolved_program: &Path,
+    resolved_program_display: &str,
+    err: std::io::Error,
+) -> anyhow::Error {
+    let mut message = if is_root_fs(root) {
+        format!("failed to execute `{resolved_program_display}`: {err}")
+    } else {
+        format!(
+            "failed to execute `chroot {} {}`: {err}",
+            root.display(),
+            resolved_program_display
+        )
+    };
+
+    if err.kind() == ErrorKind::NotFound {
+        message.push_str(&exec_not_found_diagnostics(root, resolved_program));
+    }
+
+    anyhow!(message)
+}
+
+fn exec_not_found_diagnostics(root: &Path, resolved_program: &Path) -> String {
+    let program_host_path = path_in_root(root, resolved_program);
+    let mut details = vec![
+        String::new(),
+        "exec diagnostics for ENOENT:".to_string(),
+        format!("  target program path: {}", resolved_program.display()),
+        format!("  host-visible path: {}", program_host_path.display()),
+    ];
+
+    match fs::symlink_metadata(&program_host_path) {
+        Ok(meta) => {
+            details.push(format!(
+                "  target exists: yes (mode {:o}, {} bytes)",
+                meta.permissions().mode() & 0o7777,
+                meta.len()
+            ));
+        }
+        Err(stat_err) => {
+            details.push(format!("  target exists: no ({stat_err})"));
+            return details.join("\n");
+        }
+    }
+
+    match fs::read(&program_host_path) {
+        Ok(bytes) => {
+            if let Some(interpreter) = shebang_interpreter(&bytes) {
+                details.push(format!("  script interpreter: {interpreter}"));
+                details.push(format!(
+                    "  script interpreter exists: {}",
+                    path_existence_description(root, Path::new(&interpreter))
+                ));
+            } else if is_elf(&bytes) {
+                details.push("  file format: ELF".to_string());
+                match elf_interpreter(&bytes) {
+                    Some(interpreter) => {
+                        details.push(format!("  ELF interpreter: {interpreter}"));
+                        details.push(format!(
+                            "  ELF interpreter exists: {}",
+                            path_existence_description(root, Path::new(&interpreter))
+                        ));
+                    }
+                    None => details.push("  ELF interpreter: none found".to_string()),
+                }
+            } else {
+                details.push("  file format: not ELF and no shebang".to_string());
+            }
+        }
+        Err(read_err) => details.push(format!("  failed to read target: {read_err}")),
+    }
+
+    details.join("\n")
+}
+
+fn path_existence_description(root: &Path, target_path: &Path) -> String {
+    if !target_path.is_absolute() {
+        return "not checked (interpreter path is not absolute)".to_string();
+    }
+
+    let host_path = path_in_root(root, target_path);
+    match fs::symlink_metadata(&host_path) {
+        Ok(meta) => format!(
+            "yes at {} (mode {:o}, {} bytes)",
+            host_path.display(),
+            meta.permissions().mode() & 0o7777,
+            meta.len()
+        ),
+        Err(err) => format!("no at {} ({err})", host_path.display()),
+    }
+}
+
+fn shebang_interpreter(bytes: &[u8]) -> Option<String> {
+    if !bytes.starts_with(b"#!") {
+        return None;
+    }
+
+    let line_end = bytes
+        .iter()
+        .position(|b| *b == b'\n')
+        .unwrap_or(bytes.len());
+    let line = std::str::from_utf8(&bytes[2..line_end]).ok()?.trim();
+    let interpreter = line.split_whitespace().next()?;
+    Some(interpreter.to_string())
+}
+
+fn is_elf(bytes: &[u8]) -> bool {
+    bytes.starts_with(b"\x7fELF")
+}
+
+fn elf_interpreter(bytes: &[u8]) -> Option<String> {
+    if !is_elf(bytes) || bytes.len() < 16 {
+        return None;
+    }
+
+    let class = bytes[4];
+    let data = bytes[5];
+    let little_endian = match data {
+        1 => true,
+        2 => false,
+        _ => return None,
+    };
+
+    let (phoff, phentsize, phnum) = match class {
+        1 => (
+            read_u32(bytes, 28, little_endian)? as usize,
+            read_u16(bytes, 42, little_endian)? as usize,
+            read_u16(bytes, 44, little_endian)? as usize,
+        ),
+        2 => (
+            read_u64(bytes, 32, little_endian)? as usize,
+            read_u16(bytes, 54, little_endian)? as usize,
+            read_u16(bytes, 56, little_endian)? as usize,
+        ),
+        _ => return None,
+    };
+
+    for index in 0..phnum {
+        let offset = phoff.checked_add(index.checked_mul(phentsize)?)?;
+        let header = bytes.get(offset..offset.checked_add(phentsize)?)?;
+        let p_type = read_u32(header, 0, little_endian)?;
+        if p_type != 3 {
+            continue;
+        }
+
+        let (interp_offset, interp_size) = match class {
+            1 => (
+                read_u32(header, 4, little_endian)? as usize,
+                read_u32(header, 16, little_endian)? as usize,
+            ),
+            2 => (
+                read_u64(header, 8, little_endian)? as usize,
+                read_u64(header, 32, little_endian)? as usize,
+            ),
+            _ => return None,
+        };
+        let interp_end = interp_offset.checked_add(interp_size)?;
+        let raw = bytes.get(interp_offset..interp_end)?;
+        let nul = raw.iter().position(|b| *b == 0).unwrap_or(raw.len());
+        return std::str::from_utf8(&raw[..nul]).ok().map(ToOwned::to_owned);
+    }
+
+    None
+}
+
+fn read_u16(bytes: &[u8], offset: usize, little_endian: bool) -> Option<u16> {
+    let raw: [u8; 2] = bytes.get(offset..offset.checked_add(2)?)?.try_into().ok()?;
+    Some(if little_endian {
+        u16::from_le_bytes(raw)
+    } else {
+        u16::from_be_bytes(raw)
+    })
+}
+
+fn read_u32(bytes: &[u8], offset: usize, little_endian: bool) -> Option<u32> {
+    let raw: [u8; 4] = bytes.get(offset..offset.checked_add(4)?)?.try_into().ok()?;
+    Some(if little_endian {
+        u32::from_le_bytes(raw)
+    } else {
+        u32::from_be_bytes(raw)
+    })
+}
+
+fn read_u64(bytes: &[u8], offset: usize, little_endian: bool) -> Option<u64> {
+    let raw: [u8; 8] = bytes.get(offset..offset.checked_add(8)?)?.try_into().ok()?;
+    Some(if little_endian {
+        u64::from_le_bytes(raw)
+    } else {
+        u64::from_be_bytes(raw)
+    })
+}
+
 fn resolve_target_program(root: &Path, program: &str) -> PathBuf {
     let path_env = std::env::var_os("PATH");
     resolve_target_program_with_path(root, program, path_env.as_deref())
@@ -2377,6 +2562,36 @@ CKA_TRUST_SERVER_AUTH CK_TRUST CKT_NSS_TRUSTED_DELEGATOR
         assert_eq!(resolved, PathBuf::from("missing-tool"));
     }
 
+    #[test]
+    fn shebang_interpreter_reads_first_command() {
+        let script = b"#!/usr/bin/env sh\nexit 0\n";
+
+        assert_eq!(shebang_interpreter(script).as_deref(), Some("/usr/bin/env"));
+    }
+
+    #[test]
+    fn elf_interpreter_reads_64_bit_pt_interp() {
+        let interpreter = b"/lib/ld-musl-x86_64.so.1\0";
+        let mut elf = vec![0u8; 160];
+
+        elf[0..4].copy_from_slice(b"\x7fELF");
+        elf[4] = 2; // 64-bit
+        elf[5] = 1; // little-endian
+        elf[32..40].copy_from_slice(&64u64.to_le_bytes()); // e_phoff
+        elf[54..56].copy_from_slice(&56u16.to_le_bytes()); // e_phentsize
+        elf[56..58].copy_from_slice(&1u16.to_le_bytes()); // e_phnum
+
+        elf[64..68].copy_from_slice(&3u32.to_le_bytes()); // PT_INTERP
+        elf[72..80].copy_from_slice(&128u64.to_le_bytes()); // p_offset
+        elf[96..104].copy_from_slice(&(interpreter.len() as u64).to_le_bytes()); // p_filesz
+        elf[128..128 + interpreter.len()].copy_from_slice(interpreter);
+
+        assert_eq!(
+            elf_interpreter(&elf).as_deref(),
+            Some("/lib/ld-musl-x86_64.so.1")
+        );
+    }
+
     fn unique_test_dir(name: &str) -> PathBuf {
         let nonce = SystemTime::now()
             .duration_since(UNIX_EPOCH)