diff --git a/Cargo.lock b/Cargo.lock
index 2d6b347..db1bff5 100644
--- a/Cargo.lock
+++ b/Cargo.lock
@@ -612,6 +612,12 @@ dependencies = [
  "libc",
 ]
 
+[[package]]
+name = "similar"
+version = "2.7.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "bbbb5d9659141646ae647b42fe094daf6c6192d1620870b449d9557f748b2daa"
+
 [[package]]
 name = "smallvec"
 version = "1.15.1"
@@ -705,9 +711,11 @@ dependencies = [
  "anyhow",
  "clap",
  "crossterm",
+ "regex",
  "rexpect",
  "serde",
  "serde_yaml",
+ "similar",
 ]
 
 [[package]]
diff --git a/Cargo.toml b/Cargo.toml
index 2c455a5..9db7366 100644
--- a/Cargo.toml
+++ b/Cargo.toml
@@ -10,3 +10,5 @@ rexpect = "0.7"
 anyhow = "1.0.102"
 clap = {version = "4.6", features = ["derive"]}
 crossterm = "0.29.0"
+regex = "1.10"
+similar = "2.4.0"
diff --git a/src/config.rs b/src/config.rs
index a856aec..323fa7b 100644
--- a/src/config.rs
+++ b/src/config.rs
@@ -1,4 +1,4 @@
-use serde::Deserialize;
+use serde::{Deserialize, Deserializer};
 
 #[derive(Debug, Deserialize)]
 pub struct TestConfig {
@@ -18,7 +18,25 @@ pub struct ShellInteractions {
 #[derive(Debug, Deserialize)]
 pub struct CommandTest {
     pub command: String,
-    pub expect: String,
+    #[serde(deserialize_with = "deserialize_expect")]
+    pub expect: Vec<String>,
+}
+
+fn deserialize_expect<'de, D>(deserializer: D) -> Result<Vec<String>, D::Error>
+where
+    D: Deserializer<'de>,
+{
+    #[derive(Deserialize)]
+    #[serde(untagged)]
+    enum StringOrVec {
+        String(String),
+        Vec(Vec<String>),
+    }
+
+    match StringOrVec::deserialize(deserializer)? {
+        StringOrVec::String(s) => Ok(vec![s]),
+        StringOrVec::Vec(v) => Ok(v),
+    }
 }
 
 #[cfg(test)]
diff --git a/src/engine.rs b/src/engine.rs
index 7b8cb31..530c09e 100644
--- a/src/engine.rs
+++ b/src/engine.rs
@@ -1,7 +1,10 @@
+use regex::Regex;
 use rexpect::spawn;
+use similar::{ChangeTag, TextDiff};
 
 use crate::config::TestConfig;
 use crate::traits::{Reporter, Runner};
+use crate::{RED, RESET};
 
 pub struct QemuRunner;
 
@@ -33,12 +36,27 @@ impl Runner for QemuRunner {
                 anyhow::bail!(e.to_string());
             }
 
-            if let Err(e) = p.exp_string(&test.expect) {
-                reporter.on_step_failure(
-                    &test.command,
-                    &format!("Expected '{}' not found", test.expect),
-                );
-                anyhow::bail!(e.to_string());
+            for expect in &test.expect {
+                if let Err(e) = p.exp_string(expect) {
+                    let fail_msg = match &e {
+                        rexpect::error::Error::Timeout {
+                            expected: exp, got, ..
+                        } => format_diff(exp, got),
+                        rexpect::error::Error::EOF {
+                            expected: exp, got, ..
+                        } => {
+                            format!(
+                                "EOF (OS Crashed)!\n    {RED}│{RESET} Expected: '{}'\n    {RED}│{RESET} Got:      '{}'",
+                                exp,
+                                clean_output(got)
+                            )
+                        }
+                        _ => e.to_string(),
+                    };
+
+                    reporter.on_step_failure(&test.command, &fail_msg);
+                    anyhow::bail!(e.to_string());
+                }
             }
 
             if let Err(e) = p.exp_string(&config.shell_interactions.prompt) {
@@ -58,3 +76,35 @@ impl Runner for QemuRunner {
         Ok(())
     }
 }
+
+fn clean_output(raw: &str) -> String {
+    let mut msg = raw.replace("\r\n", " ↵ ").replace('\n', " ↵ ");
+
+    if let Ok(re) = Regex::new(r"\x1b\[[0-9;]*[mK]|\\u\{1b\}\[[0-9;]*[mK]") {
+        msg = re.replace_all(&msg, "").to_string();
+    }
+    msg
+}
+
+fn format_diff(expected: &str, got: &str) -> String {
+    let clean_got = clean_output(got);
+
+    let diff = TextDiff::from_chars(expected, &clean_got);
+    let mut colored_got = String::new();
+
+    for change in diff.iter_all_changes() {
+        match change.tag() {
+            ChangeTag::Delete => {}
+            ChangeTag::Insert => {
+                colored_got.push_str(&format!("\x1b[31m{}\x1b[0m", change.value()));
+            }
+            ChangeTag::Equal => {
+                colored_got.push_str(&format!("\x1b[32m{}\x1b[0m", change.value()));
+            }
+        }
+    }
+    format!(
+        "Timeout!\n    {RED}│{RESET} Expected: '{}'\n    {RED}│{RESET} Got:      '{}'",
+        expected, colored_got
+    )
+}
diff --git a/src/lib.rs b/src/lib.rs
index 05af3d3..65025c8 100644
--- a/src/lib.rs
+++ b/src/lib.rs
@@ -2,3 +2,7 @@ pub mod config;
 pub mod engine;
 pub mod reporter;
 pub mod traits;
+
+const GREEN: &str = "\x1b[32m";
+const RED: &str = "\x1b[31m";
+const RESET: &str = "\x1b[0m";
diff --git a/src/reporter/console.rs b/src/reporter/console.rs
index ca80cb8..b997099 100644
--- a/src/reporter/console.rs
+++ b/src/reporter/console.rs
@@ -1,12 +1,9 @@
 use crate::config::TestConfig;
 use crate::traits::Reporter;
+use crate::{GREEN, RED, RESET};
 
 pub struct ConsoleReporter;
 
-const GREEN: &str = "\x1b[32m";
-const RED: &str = "\x1b[31m";
-const RESET: &str = "\x1b[0m";
-
 impl Reporter for ConsoleReporter {
     fn on_test_start(&self, config: &TestConfig) {
         println!("\n▶ 📼 WALKMAN PLAYING: {}", config.name);
diff --git a/src/reporter/tui.rs b/src/reporter/tui.rs
index 3d312a5..c834c95 100644
--- a/src/reporter/tui.rs
+++ b/src/reporter/tui.rs
@@ -6,7 +6,7 @@ use crossterm::{
     terminal::{Clear, ClearType},
 };
 
-use crate::{config::TestConfig, traits::Reporter};
+use crate::{RED, RESET, config::TestConfig, traits::Reporter};
 
 #[derive(Debug, PartialEq)]
 enum Status {
@@ -151,7 +151,7 @@ impl TuiReporter {
                 let _ = execute!(
                     out,
                     SetForegroundColor(Color::DarkGrey),
-                    Print("    │ ⌨️  Sending payload...\n"),
+                    Print("    │ 📦  Sending payload...\n"),
                     Print("    │ ⏳ Waiting for OS response...\n"),
                     ResetColor
                 );
@@ -167,8 +167,7 @@ impl TuiReporter {
                 );
                 let _ = execute!(
                     out,
-                    SetForegroundColor(Color::Red),
-                    Print(format!("    │ Reason: {}\n", reason)),
+                    Print(format!("  {RED}↳ │{RESET} Reason: {}\n", reason)),
                     ResetColor
                 );
                 lines += 1;
@@ -273,7 +272,7 @@ mod tests {
                 prompt: "$".to_string(),
                 tests: vec![CommandTest {
                     command: "ls".to_string(),
-                    expect: "file".to_string(),
+                    expect: vec!["file".to_string()],
                 }],
             },
         }