diff --git a/fuzz/fuzz_targets/fuzz_test.rs b/fuzz/fuzz_targets/fuzz_test.rs
index ff544ca2a99..c627a673c03 100644
--- a/fuzz/fuzz_targets/fuzz_test.rs
+++ b/fuzz/fuzz_targets/fuzz_test.rs
@@ -51,57 +51,128 @@ struct TestArg {
     arg_type: String,
 }
 
-fn generate_test_arg() -> String {
-    let mut rng = rand::thread_rng();
-    let test_args = vec![
+fn generate_random_path(rng: &mut dyn rand::RngCore) -> &'static str {
+    match rng.gen_range(0..=3) {
+        0 => "/dev/null",
+        1 => "/dev/random",
+        2 => "/tmp",
+        _ => "/dev/urandom",
+    }
+}
+
+fn generate_test_args() -> Vec<TestArg> {
+    vec![
         TestArg {
             arg: "-z".to_string(),
             arg_type: "STRING".to_string(),
         },
+        TestArg {
+            arg: "-n".to_string(),
+            arg_type: "STRING".to_string(),
+        },
         TestArg {
             arg: "=".to_string(),
-            arg_type: "STRING1,STRING2".to_string(),
+            arg_type: "STRING,STRING".to_string(),
+        },
+        TestArg {
+            arg: "!=".to_string(),
+            arg_type: "STRING,STRING".to_string(),
+        },
+        TestArg {
+            arg: "-eq".to_string(),
+            arg_type: "INTEGER,INTEGER".to_string(),
+        },
+        TestArg {
+            arg: "-ne".to_string(),
+            arg_type: "INTEGER,INTEGER".to_string(),
+        },
+        TestArg {
+            arg: "-gt".to_string(),
+            arg_type: "INTEGER,INTEGER".to_string(),
+        },
+        TestArg {
+            arg: "-ge".to_string(),
+            arg_type: "INTEGER,INTEGER".to_string(),
+        },
+        TestArg {
+            arg: "-lt".to_string(),
+            arg_type: "INTEGER,INTEGER".to_string(),
+        },
+        TestArg {
+            arg: "-le".to_string(),
+            arg_type: "INTEGER,INTEGER".to_string(),
+        },
+        TestArg {
+            arg: "-f".to_string(),
+            arg_type: "FILE".to_string(),
         },
-        // Add more TestArg structs for all possible arguments
-    ];
+        TestArg {
+            arg: "-d".to_string(),
+            arg_type: "FILE".to_string(),
+        },
+        TestArg {
+            arg: "-e".to_string(),
+            arg_type: "FILE".to_string(),
+        },
+        TestArg {
+            arg: "-ef".to_string(),
+            arg_type: "FILE,FILE".to_string(),
+        },
+        TestArg {
+            arg: "-nt".to_string(),
+            arg_type: "FILE,FILE".to_string(),
+        },
+    ]
+}
 
+fn generate_test_arg() -> String {
+    let mut rng = rand::thread_rng();
+    let test_args = generate_test_args();
     let mut arg = String::new();
 
-    let choice = rng.gen_range(0..=3);
+    let choice = rng.gen_range(0..=5);
 
     match choice {
         0 => {
             arg.push_str(&rng.gen_range(-100..=100).to_string());
         }
-        1 => {
+        1 | 2 | 3 => {
             let test_arg = test_args
                 .choose(&mut rng)
                 .expect("Failed to choose a random test argument");
-            arg.push_str(&test_arg.arg);
             if test_arg.arg_type.contains("INTEGER") {
-                arg.push_str(&rng.gen_range(-100..=100).to_string());
-                arg.push_str(&test_arg.arg);
-                arg.push_str(&rng.gen_range(-100..=100).to_string());
+                arg.push_str(&format!(
+                    "{} {} {}",
+                    &rng.gen_range(-100..=100).to_string(),
+                    test_arg.arg,
+                    &rng.gen_range(-100..=100).to_string()
+                ));
+            } else if test_arg.arg_type.contains("STRING,STRING") {
+                let random_str = generate_random_string(rng.gen_range(1..=10));
+                let random_str2 = generate_random_string(rng.gen_range(1..=10));
+
+                arg.push_str(&format!(
+                    "{} {} {}",
+                    &random_str, test_arg.arg, &random_str2
+                ));
             } else if test_arg.arg_type.contains("STRING") {
                 let random_str = generate_random_string(rng.gen_range(1..=10));
-                arg.push_str(&random_str);
+                arg.push_str(&format!("{} {}", test_arg.arg, &random_str));
+            } else if test_arg.arg_type.contains("FILE,FILE") {
+                let path = generate_random_path(&mut rng);
+                let path2 = generate_random_path(&mut rng);
+                arg.push_str(&format!("{} {} {}", path, test_arg.arg, path2));
             } else if test_arg.arg_type.contains("FILE") {
-                let choice = rng.gen_range(0..=2);
-                let path = match choice {
-                    0 => "/dev/null",
-                    1 => "/dev/random",
-                    _ => "/dev/urandom",
-                };
-                arg.push_str(&format!("{}{}", test_arg.arg, path));
+                let path = generate_random_path(&mut rng);
+                arg.push_str(&format!("{} {}", test_arg.arg, path));
             }
         }
-        2 => {
+        4 => {
             let random_str = generate_random_string(rng.gen_range(1..=10));
             arg.push_str(&random_str);
         }
         _ => {
-            let choice = rng.gen_range(0..=2);
-            let path = match choice {
+            let path = match rng.gen_range(0..=2) {
                 0 => "/dev/null",
                 1 => "/dev/random",
                 _ => "/dev/urandom",
@@ -192,6 +263,7 @@ fuzz_target!(|_data: &[u8]| {
                 println!("GNU output: {}", gnu_output);
                 println!("My exit status: {}", uumain_exit_status);
                 println!("GNU exit status: {}", gnu_exit_status);
+                panic!();
             } else {
                 println!(
                     "Outputs and exit statuses matched for expression {:?}",