diff --git a/crates/goose-cli/src/commands/session.rs b/crates/goose-cli/src/commands/session.rs
index 6a36d61d..5d8f8bed 100644
--- a/crates/goose-cli/src/commands/session.rs
+++ b/crates/goose-cli/src/commands/session.rs
@@ -3,20 +3,27 @@ use goose::session::info::{get_session_info, SessionInfo, SortOrder};
 use regex::Regex;
 use std::fs;
 
-pub fn remove_session(session: &SessionInfo) -> Result<()> {
-    let should_delete = cliclack::confirm(format!(
-        "Are you sure you want to delete session `{}`? (yes/no):?",
-        session.id
-    ))
-    .initial_value(true)
-    .interact()?;
-    if should_delete {
-        fs::remove_file(session.path.clone())
-            .with_context(|| format!("Failed to remove session file '{}'", session.path))?;
-        println!("Session `{}` removed.", session.id);
-    } else {
-        println!("Skipping deletion of '{}'.", session.id);
+pub fn remove_sessions(sessions: Vec<SessionInfo>) -> Result<()> {
+    println!("The following sessions will be removed:");
+    for session in &sessions {
+        println!("- {}", session.id);
     }
+
+    let should_delete =
+        cliclack::confirm("Are you sure you want to delete all these sessions? (yes/no):")
+            .initial_value(true)
+            .interact()?;
+
+    if should_delete {
+        for session in sessions {
+            fs::remove_file(session.path.clone())
+                .with_context(|| format!("Failed to remove session file '{}'", session.path))?;
+            println!("Session `{}` removed.", session.id);
+        }
+    } else {
+        println!("Skipping deletion of the sessions.");
+    }
+
     Ok(())
 }
 
@@ -24,37 +31,38 @@ pub fn handle_session_remove(id: String, regex_string: String) -> Result<()> {
     let sessions = match get_session_info(SortOrder::Descending) {
         Ok(sessions) => sessions,
         Err(e) => {
-            tracing::error!("Failed to remove sessions: {:?}", e);
-            return Err(anyhow::anyhow!("Failed to remove sessions"));
+            tracing::error!("Failed to retrieve sessions: {:?}", e);
+            return Err(anyhow::anyhow!("Failed to retrieve sessions"));
         }
     };
+
+    let matched_sessions: Vec<SessionInfo>;
     if !id.is_empty() {
-        if let Some(session_to_remove) = sessions.iter().find(|s| s.id == id) {
-            remove_session(session_to_remove)?;
+        if let Some(session) = sessions.iter().find(|s| s.id == id) {
+            matched_sessions = vec![session.clone()];
         } else {
             return Err(anyhow::anyhow!("Session '{}' not found.", id));
         }
     } else if !regex_string.is_empty() {
-        let session_regex: Regex = Regex::new(regex_string.as_str())?;
-        let mut removed_count = 0;
-        for session_info in sessions {
-            if session_regex.is_match(session_info.id.as_str()) {
-                remove_session(&session_info)?;
-                removed_count += 1;
-            }
-        }
-        if removed_count == 0 {
+        let session_regex = Regex::new(&regex_string)
+            .with_context(|| format!("Invalid regex pattern '{}'", regex_string))?;
+        matched_sessions = sessions
+            .into_iter()
+            .filter(|session| session_regex.is_match(&session.id))
+            .collect();
+
+        if matched_sessions.is_empty() {
             println!(
                 "Regex string '{}' does not match any sessions",
                 regex_string
             );
+            return Ok(());
         }
     } else {
-        return Err(anyhow::anyhow!(
-            "Neither --regex nor --session-name flags provided."
-        ));
+        return Err(anyhow::anyhow!("Neither --regex nor --id flags provided."));
     }
-    Ok(())
+
+    remove_sessions(matched_sessions)
 }
 
 pub fn handle_session_list(verbose: bool, format: String, ascending: bool) -> Result<()> {
diff --git a/crates/goose/src/session/info.rs b/crates/goose/src/session/info.rs
index 44c2ca4f..f44794d3 100644
--- a/crates/goose/src/session/info.rs
+++ b/crates/goose/src/session/info.rs
@@ -4,7 +4,7 @@ use std::cmp::Ordering;
 
 use crate::session::{self, SessionMetadata};
 
-#[derive(Serialize)]
+#[derive(Clone, Serialize)]
 pub struct SessionInfo {
     pub id: String,
     pub path: String,