diff --git a/eh/src/error.rs b/eh/src/error.rs
index 173f047..403e2d1 100644
--- a/eh/src/error.rs
+++ b/eh/src/error.rs
@@ -1,9 +1,11 @@
+use std::time::Duration;
+
 use thiserror::Error;
 
 #[derive(Error, Debug)]
 pub enum EhError {
-  #[error("Nix command failed: {0}")]
-  NixCommandFailed(String),
+  #[error("Nix command 'nix {command}' failed")]
+  NixCommandFailed { command: String },
 
   #[error("IO error: {0}")]
   Io(#[from] std::io::Error),
@@ -14,10 +16,10 @@ pub enum EhError {
   #[error("UTF-8 conversion error: {0}")]
   Utf8(#[from] std::string::FromUtf8Error),
 
-  #[error("Hash extraction failed")]
-  HashExtractionFailed,
+  #[error("Hash extraction failed: could not parse hash from nix output")]
+  HashExtractionFailed { stderr: String },
 
-  #[error("No Nix files found")]
+  #[error("No Nix files found in the current directory")]
   NoNixFilesFound,
 
   #[error("Failed to fix hash in file: {path}")]
@@ -29,6 +31,18 @@ pub enum EhError {
   #[error("Command execution failed: {command}")]
   CommandFailed { command: String },
 
+  #[error("Command '{command}' timed out after {} seconds", duration.as_secs())]
+  Timeout {
+    command:  String,
+    duration: Duration,
+  },
+
+  #[error("Pre-evaluation of '{expression}' failed: {stderr}")]
+  PreEvalFailed {
+    expression: String,
+    stderr:     String,
+  },
+
   #[error("Invalid input: {input} - {reason}")]
   InvalidInput { input: String, reason: String },
 }
@@ -40,15 +54,190 @@ impl EhError {
   pub const fn exit_code(&self) -> i32 {
     match self {
       Self::ProcessExit { code } => *code,
-      Self::NixCommandFailed(_) => 2,
+      Self::NixCommandFailed { .. } => 2,
       Self::CommandFailed { .. } => 3,
-      Self::HashExtractionFailed => 4,
+      Self::HashExtractionFailed { .. } => 4,
       Self::NoNixFilesFound => 5,
       Self::HashFixFailed { .. } => 6,
       Self::InvalidInput { .. } => 7,
       Self::Io(_) => 8,
       Self::Regex(_) => 9,
       Self::Utf8(_) => 10,
+      Self::Timeout { .. } => 11,
+      Self::PreEvalFailed { .. } => 12,
+    }
+  }
+
+  #[must_use]
+  pub fn hint(&self) -> Option<&str> {
+    match self {
+      Self::NixCommandFailed { .. } => {
+        Some("Run with --show-trace for more details from nix")
+      },
+      Self::PreEvalFailed { .. } => {
+        Some(
+          "Check that the expression exists in the flake and is spelled \
+           correctly",
+        )
+      },
+      Self::HashExtractionFailed { .. } => {
+        Some(
+          "The nix output contained a hash mismatch but the hash could not be \
+           parsed",
+        )
+      },
+      Self::NoNixFilesFound => {
+        Some("Run this command from a directory containing .nix files")
+      },
+      Self::Timeout { .. } => {
+        Some(
+          "The command took too long; try a faster network or a smaller \
+           derivation",
+        )
+      },
+      Self::InvalidInput { .. } => {
+        Some("Avoid shell metacharacters in nix arguments")
+      },
+      Self::Io(_)
+      | Self::Regex(_)
+      | Self::Utf8(_)
+      | Self::HashFixFailed { .. }
+      | Self::ProcessExit { .. }
+      | Self::CommandFailed { .. } => None,
     }
   }
 }
+
+#[cfg(test)]
+mod tests {
+  use super::*;
+
+  #[test]
+  fn test_exit_codes() {
+    assert_eq!(
+      EhError::NixCommandFailed {
+        command: "build".into(),
+      }
+      .exit_code(),
+      2
+    );
+    assert_eq!(
+      EhError::CommandFailed {
+        command: "x".into(),
+      }
+      .exit_code(),
+      3
+    );
+    assert_eq!(
+      EhError::HashExtractionFailed {
+        stderr: String::new(),
+      }
+      .exit_code(),
+      4
+    );
+    assert_eq!(EhError::NoNixFilesFound.exit_code(), 5);
+    assert_eq!(EhError::HashFixFailed { path: "x".into() }.exit_code(), 6);
+    assert_eq!(
+      EhError::InvalidInput {
+        input:  "x".into(),
+        reason: "y".into(),
+      }
+      .exit_code(),
+      7
+    );
+    assert_eq!(
+      EhError::Timeout {
+        command:  "build".into(),
+        duration: Duration::from_secs(300),
+      }
+      .exit_code(),
+      11
+    );
+    assert_eq!(
+      EhError::PreEvalFailed {
+        expression: "x".into(),
+        stderr:     "y".into(),
+      }
+      .exit_code(),
+      12
+    );
+    assert_eq!(EhError::ProcessExit { code: 42 }.exit_code(), 42);
+  }
+
+  #[test]
+  fn test_display_messages() {
+    let err = EhError::Timeout {
+      command:  "build".into(),
+      duration: Duration::from_secs(300),
+    };
+    assert_eq!(
+      err.to_string(),
+      "Command 'build' timed out after 300 seconds"
+    );
+
+    let err = EhError::PreEvalFailed {
+      expression: "nixpkgs#hello".into(),
+      stderr:     "attribute not found".into(),
+    };
+    assert!(err.to_string().contains("nixpkgs#hello"));
+    assert!(err.to_string().contains("attribute not found"));
+
+    let err = EhError::HashExtractionFailed {
+      stderr: "some output".into(),
+    };
+    assert!(err.to_string().contains("could not parse hash"));
+  }
+
+  #[test]
+  fn test_hints() {
+    assert!(
+      EhError::PreEvalFailed {
+        expression: "x".into(),
+        stderr:     "y".into(),
+      }
+      .hint()
+      .is_some()
+    );
+    assert!(
+      EhError::HashExtractionFailed {
+        stderr: String::new(),
+      }
+      .hint()
+      .is_some()
+    );
+    assert!(EhError::NoNixFilesFound.hint().is_some());
+    assert!(
+      EhError::Timeout {
+        command:  "x".into(),
+        duration: Duration::from_secs(1),
+      }
+      .hint()
+      .is_some()
+    );
+    assert!(
+      EhError::InvalidInput {
+        input:  "x".into(),
+        reason: "y".into(),
+      }
+      .hint()
+      .is_some()
+    );
+    // Variants with hints
+    assert!(
+      EhError::NixCommandFailed {
+        command: "build".into(),
+      }
+      .hint()
+      .is_some()
+    );
+    // Variants without hints
+    assert!(
+      EhError::CommandFailed {
+        command: "x".into(),
+      }
+      .hint()
+      .is_none()
+    );
+    assert!(EhError::ProcessExit { code: 1 }.hint().is_none());
+  }
+}