diff --git a/src/handlers/accounts.rs b/src/handlers/accounts.rs
index b55b9b8..697e144 100644
--- a/src/handlers/accounts.rs
+++ b/src/handlers/accounts.rs
@@ -12,6 +12,7 @@ use crate::{
     crypto::{generate_salt, hash_password_for_storage},
     db,
     error::AppError,
+    handlers::attachments,
     models::{
         cipher::CipherData,
         sync::Profile,
@@ -477,6 +478,12 @@ pub async fn delete_account(
         return Err(AppError::Unauthorized("Invalid password".to_string()));
     }
 
+    if attachments::attachments_enabled(env.as_ref()) {
+        let bucket = attachments::require_bucket(env.as_ref())?;
+        let keys = attachments::list_attachment_keys_for_user(&db, user_id).await?;
+        attachments::delete_r2_objects(&bucket, &keys).await?;
+    }
+
     // Delete all user's ciphers
     query!(&db, "DELETE FROM ciphers WHERE user_id = ?1", user_id)
         .map_err(|_| AppError::Database)?
diff --git a/src/handlers/attachments.rs b/src/handlers/attachments.rs
index 46beb22..e57aa0d 100644
--- a/src/handlers/attachments.rs
+++ b/src/handlers/attachments.rs
@@ -81,6 +81,12 @@ pub struct AttachmentDownloadQuery {
     pub token: Option<String>,
 }
 
+#[derive(Deserialize)]
+struct AttachmentKeyRow {
+    cipher_id: String,
+    id: String,
+}
+
 impl NumberOrString {
     pub fn into_i64(self) -> Result<i64, AppError> {
         match self {
@@ -368,12 +374,7 @@ pub async fn delete_attachment(
     }
 
     // Delete R2 object; ignore missing objects
-    if let Err(err) = bucket.delete(attachment.r2_key()).await {
-        let msg = err.to_string();
-        if !(msg.contains("NoSuchKey") || msg.contains("404") || msg.contains("NotFound")) {
-            return Err(AppError::Worker(err));
-        }
-    }
+    delete_r2_objects(&bucket, &[attachment.r2_key()]).await?;
 
     query!(&db, "DELETE FROM attachments WHERE id = ?1", attachment.id)
         .map_err(|_| AppError::Database)?
@@ -521,15 +522,111 @@ pub async fn hydrate_ciphers_attachments(
     Ok(())
 }
 
-fn attachments_enabled(env: &Env) -> bool {
+pub(crate) fn attachments_enabled(env: &Env) -> bool {
     env.bucket(ATTACHMENTS_BUCKET).is_ok()
 }
 
-fn require_bucket(env: &Env) -> Result<Bucket, AppError> {
+pub(crate) fn require_bucket(env: &Env) -> Result<Bucket, AppError> {
     env.bucket(ATTACHMENTS_BUCKET)
         .map_err(|_| AppError::BadRequest("Attachments are not enabled".to_string()))
 }
 
+fn is_not_found_error(err: &worker::Error) -> bool {
+    let msg = err.to_string();
+    msg.contains("NoSuchKey") || msg.contains("404") || msg.contains("NotFound")
+}
+
+pub(crate) async fn delete_r2_objects(
+    bucket: &Bucket,
+    keys: &[String],
+) -> Result<(), AppError> {
+    for key in keys {
+        if let Err(err) = bucket.delete(key).await {
+            if !is_not_found_error(&err) {
+                return Err(AppError::Worker(err));
+            }
+        }
+    }
+    Ok(())
+}
+
+fn map_rows_to_keys(rows: Vec<AttachmentKeyRow>) -> Vec<String> {
+    rows.into_iter()
+        .map(|row| format!("{}/{}", row.cipher_id, row.id))
+        .collect()
+}
+
+pub(crate) async fn list_attachment_keys_for_cipher_ids(
+    db: &D1Database,
+    cipher_ids: &[String],
+    user_id: Option<&str>,
+) -> Result<Vec<String>, AppError> {
+    if cipher_ids.is_empty() {
+        return Ok(Vec::new());
+    }
+
+    let ids_json = serde_json::to_string(cipher_ids).map_err(|_| AppError::Internal)?;
+
+    let mut sql = "SELECT a.cipher_id, a.id FROM attachments a JOIN ciphers c ON a.cipher_id = c.id WHERE c.id IN (SELECT value FROM json_each(?1))".to_string();
+    let mut params: Vec<worker::wasm_bindgen::JsValue> = vec![ids_json.into()];
+
+    if let Some(uid) = user_id {
+        sql.push_str(" AND c.user_id = ?2");
+        params.push(uid.into());
+    }
+
+    let rows: Vec<AttachmentKeyRow> = db
+        .prepare(&sql)
+        .bind(&params)?
+        .all()
+        .await
+        .map_err(|_| AppError::Database)?
+        .results()
+        .map_err(|_| AppError::Database)?;
+
+    Ok(map_rows_to_keys(rows))
+}
+
+pub(crate) async fn list_attachment_keys_for_user(
+    db: &D1Database,
+    user_id: &str,
+) -> Result<Vec<String>, AppError> {
+    let rows: Vec<AttachmentKeyRow> = db
+        .prepare(
+            "SELECT a.cipher_id, a.id FROM attachments a \
+             JOIN ciphers c ON a.cipher_id = c.id \
+             WHERE c.user_id = ?1",
+        )
+        .bind(&[user_id.into()])?
+        .all()
+        .await
+        .map_err(|_| AppError::Database)?
+        .results()
+        .map_err(|_| AppError::Database)?;
+
+    Ok(map_rows_to_keys(rows))
+}
+
+pub(crate) async fn list_attachment_keys_for_soft_deleted_before(
+    db: &D1Database,
+    cutoff_exclusive: &str,
+) -> Result<Vec<String>, AppError> {
+    let rows: Vec<AttachmentKeyRow> = db
+        .prepare(
+            "SELECT a.cipher_id, a.id FROM attachments a \
+             JOIN ciphers c ON a.cipher_id = c.id \
+             WHERE c.deleted_at IS NOT NULL AND c.deleted_at < ?1",
+        )
+        .bind(&[cutoff_exclusive.into()])?
+        .all()
+        .await
+        .map_err(|_| AppError::Database)?
+        .results()
+        .map_err(|_| AppError::Database)?;
+
+    Ok(map_rows_to_keys(rows))
+}
+
 fn upload_url(cipher_id: &str, attachment_id: &str) -> String {
     format!("/api/ciphers/{cipher_id}/attachment/{attachment_id}")
 }
diff --git a/src/handlers/ciphers.rs b/src/handlers/ciphers.rs
index 74c76db..f7d0485 100644
--- a/src/handlers/ciphers.rs
+++ b/src/handlers/ciphers.rs
@@ -416,6 +416,12 @@ pub async fn hard_delete_cipher(
 ) -> Result<Json<()>, AppError> {
     let db = db::get_db(&env)?;
 
+    if attachments::attachments_enabled(env.as_ref()) {
+        let bucket = attachments::require_bucket(env.as_ref())?;
+        let keys = attachments::list_attachment_keys_for_cipher_ids(&db, &[id.clone()], Some(&claims.sub)).await?;
+        attachments::delete_r2_objects(&bucket, &keys).await?;
+    }
+
     query!(
         &db,
         "DELETE FROM ciphers WHERE id = ?1 AND user_id = ?2",
@@ -440,9 +446,18 @@ pub async fn hard_delete_ciphers_bulk(
 ) -> Result<Json<()>, AppError> {
     let db = db::get_db(&env)?;
     let batch_size = get_batch_size(&env);
-    let mut statements: Vec<D1PreparedStatement> = Vec::with_capacity(payload.ids.len());
+    let ids = payload.ids;
 
-    for id in payload.ids {
+    if attachments::attachments_enabled(env.as_ref()) {
+        let bucket = attachments::require_bucket(env.as_ref())?;
+        let keys =
+            attachments::list_attachment_keys_for_cipher_ids(&db, &ids, Some(&claims.sub)).await?;
+        attachments::delete_r2_objects(&bucket, &keys).await?;
+    }
+
+    let mut statements: Vec<D1PreparedStatement> = Vec::with_capacity(ids.len());
+
+    for id in ids {
         let stmt = query!(
             &db,
             "DELETE FROM ciphers WHERE id = ?1 AND user_id = ?2",
@@ -747,6 +762,12 @@ pub async fn purge_vault(
         return Err(AppError::Unauthorized("Invalid password".to_string()));
     }
 
+    if attachments::attachments_enabled(env.as_ref()) {
+        let bucket = attachments::require_bucket(env.as_ref())?;
+        let keys = attachments::list_attachment_keys_for_user(&db, user_id).await?;
+        attachments::delete_r2_objects(&bucket, &keys).await?;
+    }
+
     // Delete all user's ciphers (both active and soft-deleted)
     query!(&db, "DELETE FROM ciphers WHERE user_id = ?1", user_id)
         .map_err(|_| AppError::Database)?
diff --git a/src/handlers/purge.rs b/src/handlers/purge.rs
index 6e7b59e..320fc4f 100644
--- a/src/handlers/purge.rs
+++ b/src/handlers/purge.rs
@@ -5,6 +5,7 @@
 //! retention period.
 
 use chrono::{Duration, Utc};
+use crate::handlers::attachments;
 use std::collections::HashSet;
 use worker::{query, D1Database, Env};
 
@@ -78,6 +79,18 @@ pub async fn purge_deleted_ciphers(env: &Env) -> Result<u32, worker::Error> {
     let count = count_result.map(|r| r.count).unwrap_or(0);
 
     if count > 0 {
+        if attachments::attachments_enabled(env) {
+            let bucket = attachments::require_bucket(env)
+                .map_err(|e| worker::Error::RustError(e.to_string()))?;
+            let keys = attachments::list_attachment_keys_for_soft_deleted_before(&db, &cutoff_str)
+                .await
+                .map_err(|e| worker::Error::RustError(e.to_string()))?;
+
+            attachments::delete_r2_objects(&bucket, &keys)
+                .await
+                .map_err(|e| worker::Error::RustError(e.to_string()))?;
+        }
+
         // Delete the records
         query!(
             &db,