diff --git a/src/assertions/file.rs b/src/assertions/file.rs
index 41dc94d..9be518c 100644
--- a/src/assertions/file.rs
+++ b/src/assertions/file.rs
@@ -43,14 +43,39 @@ pub fn check_file_content(
 }
 
 /// Check if workspace file exists
-pub fn check_workspace_file(work_dir: &Path, file_path: &str) -> Result<(), String> {
+pub fn check_workspace_file(
+    work_dir: &Path,
+    file_path: &str,
+    copy_to_output: bool,
+    log_output_dir: Option<&Path>,
+) -> Result<(), String> {
     let full_path = work_dir.join(file_path);
 
-    if full_path.exists() && full_path.is_file() {
-        Ok(())
-    } else {
-        Err(format!("Workspace file '{}' does not exist", file_path))
+    if !(full_path.exists() && full_path.is_file()) {
+        return Err(format!("Workspace file '{}' does not exist", file_path));
+    }
+
+    // Copy file to output directory if requested
+    if copy_to_output {
+        if let Some(output_dir) = log_output_dir {
+            if let Err(e) = copy_file_to_dir(&full_path, file_path, output_dir) {
+                return Err(format!("Failed to copy '{}' to output: {}", file_path, e));
+            }
+        }
     }
+
+    Ok(())
+}
+
+/// Copy a file to the output directory, preserving its relative path structure
+fn copy_file_to_dir(source: &Path, relative_path: &str, output_dir: &Path) -> std::io::Result<()> {
+    std::fs::create_dir_all(output_dir)?;
+    let dest = output_dir.join(relative_path);
+    if let Some(parent) = dest.parent() {
+        std::fs::create_dir_all(parent)?;
+    }
+    std::fs::copy(source, &dest)?;
+    Ok(())
 }
 
 /// Check if workspace directory exists
diff --git a/src/assertions/mod.rs b/src/assertions/mod.rs
index 6539ebb..ca6b225 100644
--- a/src/assertions/mod.rs
+++ b/src/assertions/mod.rs
@@ -23,15 +23,17 @@ pub struct AssertionChecker {
     #[cfg(not(test))]
     log_data: Vec<Value>,
     work_dir: std::path::PathBuf,
+    log_output_dir: Option<std::path::PathBuf>,
 }
 
 impl AssertionChecker {
     /// Create a new assertion checker
-    pub fn new(log_file: &Path, work_dir: &Path) -> Self {
+    pub fn new(log_file: &Path, work_dir: &Path, log_output_dir: Option<&Path>) -> Self {
         let log_data = Self::load_log_file(log_file);
         Self {
             log_data,
             work_dir: work_dir.to_path_buf(),
+            log_output_dir: log_output_dir.map(|p| p.to_path_buf()),
         }
     }
 
@@ -71,7 +73,12 @@ impl AssertionChecker {
         let result = match cmd.as_str() {
             "workspace-file" => {
                 let path = check.command.path.as_ref().ok_or("Missing path")?;
-                file::check_workspace_file(&self.work_dir, path)
+                file::check_workspace_file(
+                    &self.work_dir,
+                    path,
+                    check.command.copy_to_output.unwrap_or(false),
+                    self.log_output_dir.as_deref(),
+                )
             }
             "workspace-dir" => {
                 let path = check.command.path.as_ref().ok_or("Missing path")?;
diff --git a/src/assertions/tests.rs b/src/assertions/tests.rs
index e1fc615..7623c46 100644
--- a/src/assertions/tests.rs
+++ b/src/assertions/tests.rs
@@ -8,7 +8,7 @@ mod tests {
     fn create_checker(log_file: &str) -> AssertionChecker {
         let log_path = Path::new(log_file);
         let work_dir = tempfile::tempdir().unwrap();
-        AssertionChecker::new(log_path, work_dir.path())
+        AssertionChecker::new(log_path, work_dir.path(), None)
     }
 
     #[test]
@@ -132,11 +132,20 @@ mod tests {
         let test_file = work_dir.path().join("output.txt");
         std::fs::write(&test_file, "test content").unwrap();
 
-        let result = crate::assertions::file::check_workspace_file(work_dir.path(), "output.txt");
+        let result = crate::assertions::file::check_workspace_file(
+            work_dir.path(),
+            "output.txt",
+            false,
+            None,
+        );
         assert!(result.is_ok(), "workspace file should exist");
 
-        let result =
-            crate::assertions::file::check_workspace_file(work_dir.path(), "nonexistent.txt");
+        let result = crate::assertions::file::check_workspace_file(
+            work_dir.path(),
+            "nonexistent.txt",
+            false,
+            None,
+        );
         assert!(result.is_err(), "nonexistent file should not exist");
     }
 
@@ -188,7 +197,7 @@ mod tests {
         let empty_log = work_dir.path().join("empty.log");
         std::fs::write(&empty_log, "").unwrap();
 
-        let checker = AssertionChecker::new(&empty_log, work_dir.path());
+        let checker = AssertionChecker::new(&empty_log, work_dir.path(), None);
         let init = checker.init_message();
         assert!(init.is_none(), "empty log should not have init message");
     }
@@ -244,7 +253,7 @@ mod tests {
         let nonexistent_log = work_dir.path().join("nonexistent.log");
 
         // Should not panic, just return empty checker
-        let checker = AssertionChecker::new(&nonexistent_log, work_dir.path());
+        let checker = AssertionChecker::new(&nonexistent_log, work_dir.path(), None);
         assert_eq!(
             checker.log_data.len(),
             0,
diff --git a/src/models/check.rs b/src/models/check.rs
index 9dad9c5..4f4dc1b 100644
--- a/src/models/check.rs
+++ b/src/models/check.rs
@@ -44,4 +44,6 @@ pub struct CheckData {
     pub query: Option<String>,
     #[serde(default)]
     pub deny: Option<bool>,
+    #[serde(default)]
+    pub copy_to_output: Option<bool>,
 }
diff --git a/src/runtime/executor.rs b/src/runtime/executor.rs
index aeb0265..8ab9e49 100644
--- a/src/runtime/executor.rs
+++ b/src/runtime/executor.rs
@@ -155,7 +155,8 @@ impl TestExecutor {
         }
 
         // Run assertions
-        let checker = AssertionChecker::new(&log_path, workspace.path());
+        let checker =
+            AssertionChecker::new(&log_path, workspace.path(), self.log_output_dir.as_deref());
         let check_results: Vec<CheckResult> = desc
             .test
             .checks