diff --git a/crates/schema/database/mysql_queries/src/queries/user_impersonation_requests/lookup_user_impersonation_request.rs b/crates/schema/database/mysql_queries/src/queries/user_impersonation_requests/lookup_user_impersonation_request.rs
new file mode 100644
index 0000000000..c99f46f59d
--- /dev/null
+++ b/crates/schema/database/mysql_queries/src/queries/user_impersonation_requests/lookup_user_impersonation_request.rs
@@ -0,0 +1,51 @@
+use chrono::{DateTime, Utc};
+use sqlx::{FromRow, MySqlPool, Row};
+
+use tokens::tokens::users::UserToken;
+
+pub struct UserImpersonationRequestRecord {
+  pub token: String,
+  pub impersonated_user_token: UserToken,
+  pub impersonator_user_token: UserToken,
+  pub public_impersonation_token: String,
+  pub is_redeemed: bool,
+  pub expires_at: DateTime<Utc>,
+}
+
+/// Look up a user impersonation request by the public impersonation token (the "password").
+pub async fn lookup_user_impersonation_request(
+  public_impersonation_token: &str,
+  mysql_pool: &MySqlPool,
+) -> Result<Option<UserImpersonationRequestRecord>, sqlx::Error> {
+  let maybe_row = sqlx::query(
+    r#"
+SELECT
+  token,
+  impersonated_user_token,
+  impersonator_user_token,
+  public_impersonation_token,
+  is_redeemed,
+  expires_at
+FROM user_impersonation_requests
+WHERE public_impersonation_token = ?
+LIMIT 1
+    "#,
+  )
+    .bind(public_impersonation_token)
+    .fetch_optional(mysql_pool)
+    .await?;
+
+  let row = match maybe_row {
+    Some(row) => row,
+    None => return Ok(None),
+  };
+
+  Ok(Some(UserImpersonationRequestRecord {
+    token: row.get("token"),
+    impersonated_user_token: UserToken::new_from_str(row.get("impersonated_user_token")),
+    impersonator_user_token: UserToken::new_from_str(row.get("impersonator_user_token")),
+    public_impersonation_token: row.get("public_impersonation_token"),
+    is_redeemed: row.get("is_redeemed"),
+    expires_at: row.get("expires_at"),
+  }))
+}
diff --git a/crates/schema/database/mysql_queries/src/queries/user_impersonation_requests/mark_impersonation_token_as_redeemed.rs b/crates/schema/database/mysql_queries/src/queries/user_impersonation_requests/mark_impersonation_token_as_redeemed.rs
new file mode 100644
index 0000000000..9950a14ad6
--- /dev/null
+++ b/crates/schema/database/mysql_queries/src/queries/user_impersonation_requests/mark_impersonation_token_as_redeemed.rs
@@ -0,0 +1,35 @@
+use std::marker::PhantomData;
+
+use sqlx::{Executor, MySql};
+
+pub struct MarkImpersonationTokenAsRedeemedArgs<'a, 'c: 'a, E>
+  where E: 'a + Executor<'c, Database = MySql>
+{
+  pub public_impersonation_token: &'a str,
+  pub ip_address_redemption: &'a str,
+
+  pub mysql_executor: E,
+  pub phantom: PhantomData<&'c E>,
+}
+
+pub async fn mark_impersonation_token_as_redeemed<'a, 'c, E>(
+  args: MarkImpersonationTokenAsRedeemedArgs<'a, 'c, E>,
+) -> Result<(), sqlx::Error>
+  where E: 'a + Executor<'c, Database = MySql>
+{
+  sqlx::query(
+    r#"
+UPDATE user_impersonation_requests
+SET
+  is_redeemed = TRUE,
+  ip_address_redemption = ?
+WHERE public_impersonation_token = ?
+    "#,
+  )
+    .bind(args.ip_address_redemption)
+    .bind(args.public_impersonation_token)
+    .execute(args.mysql_executor)
+    .await?;
+
+  Ok(())
+}
diff --git a/crates/schema/database/mysql_queries/src/queries/user_impersonation_requests/mod.rs b/crates/schema/database/mysql_queries/src/queries/user_impersonation_requests/mod.rs
index 6b582f6f70..72dbbdfac9 100644
--- a/crates/schema/database/mysql_queries/src/queries/user_impersonation_requests/mod.rs
+++ b/crates/schema/database/mysql_queries/src/queries/user_impersonation_requests/mod.rs
@@ -1 +1,3 @@
 pub mod insert_user_impersonation_request;
+pub mod lookup_user_impersonation_request;
+pub mod mark_impersonation_token_as_redeemed;
diff --git a/crates/schema/database/mysql_queries/src/queries/users/user_sessions/create_impersonated_user_session.rs b/crates/schema/database/mysql_queries/src/queries/users/user_sessions/create_impersonated_user_session.rs
new file mode 100644
index 0000000000..b194d36e8c
--- /dev/null
+++ b/crates/schema/database/mysql_queries/src/queries/users/user_sessions/create_impersonated_user_session.rs
@@ -0,0 +1,53 @@
+use std::marker::PhantomData;
+
+use chrono::{DateTime, Utc};
+use sqlx::{Executor, MySql};
+
+use tokens::tokens::user_sessions::UserSessionToken;
+use tokens::tokens::users::UserToken;
+
+pub struct CreateImpersonatedUserSessionArgs<'a, 'c: 'a, E>
+  where E: 'a + Executor<'c, Database = MySql>
+{
+  /// The user being impersonated (the session will act as this user).
+  pub user_token: &'a UserToken,
+
+  /// The staff/moderator user who initiated the impersonation.
+  pub impersonator_user_token: &'a UserToken,
+
+  pub ip_address: &'a str,
+  pub expires_at: DateTime<Utc>,
+
+  pub mysql_executor: E,
+  pub phantom: PhantomData<&'c E>,
+}
+
+pub async fn create_impersonated_user_session<'a, 'c, E>(
+  args: CreateImpersonatedUserSessionArgs<'a, 'c, E>,
+) -> Result<UserSessionToken, sqlx::Error>
+  where E: 'a + Executor<'c, Database = MySql>
+{
+  let session_token = UserSessionToken::generate();
+
+  sqlx::query(
+    r#"
+INSERT INTO user_sessions (
+  token,
+  user_token,
+  maybe_impersonation_user_token,
+  ip_address_creation,
+  expires_at
+)
+VALUES (?, ?, ?, ?, ?)
+    "#,
+  )
+    .bind(session_token.as_str())
+    .bind(args.user_token.as_str())
+    .bind(args.impersonator_user_token.as_str())
+    .bind(args.ip_address)
+    .bind(args.expires_at)
+    .execute(args.mysql_executor)
+    .await?;
+
+  Ok(session_token)
+}
diff --git a/crates/schema/database/mysql_queries/src/queries/users/user_sessions/mod.rs b/crates/schema/database/mysql_queries/src/queries/users/user_sessions/mod.rs
index a591ae7554..bf2073a9d1 100644
--- a/crates/schema/database/mysql_queries/src/queries/users/user_sessions/mod.rs
+++ b/crates/schema/database/mysql_queries/src/queries/users/user_sessions/mod.rs
@@ -1,3 +1,4 @@
+pub mod create_impersonated_user_session;
 pub mod create_user_session;
 pub mod create_user_session_with_transactor;
 pub mod delete_user_session;
diff --git a/crates/service/web/storyteller_web/src/http_server/endpoints/users/login_handler.rs b/crates/service/web/storyteller_web/src/http_server/endpoints/users/login_handler.rs
index 5a8db5c8ab..f1a9a77419 100644
--- a/crates/service/web/storyteller_web/src/http_server/endpoints/users/login_handler.rs
+++ b/crates/service/web/storyteller_web/src/http_server/endpoints/users/login_handler.rs
@@ -1,15 +1,29 @@
 use std::fmt;
 use std::fmt::Formatter;
+use std::marker::PhantomData;
 
 use actix_artcraft::sessions::user_sessions::http_user_session_manager::HttpUserSessionManager;
 use actix_web::error::ResponseError;
 use actix_web::http::StatusCode;
 use actix_web::{web, HttpRequest, HttpResponse};
+use chrono::{Duration, Utc};
+use enums::by_table::staff_audit_logs::staff_audit_action::StaffAuditAction;
+use enums::by_table::staff_audit_logs::staff_audit_entity_type::StaffAuditEntityType;
 use http_server_common::request::get_request_ip::get_request_ip;
 use http_server_common::response::serialize_as_json_error::serialize_as_json_error;
 use log::{info, warn};
+use mysql_queries::queries::staff_audit_logs::insert_staff_audit_log::{
+  insert_staff_audit_log, InsertStaffAuditLogArgs,
+};
+use mysql_queries::queries::user_impersonation_requests::lookup_user_impersonation_request::lookup_user_impersonation_request;
+use mysql_queries::queries::user_impersonation_requests::mark_impersonation_token_as_redeemed::{
+  mark_impersonation_token_as_redeemed, MarkImpersonationTokenAsRedeemedArgs,
+};
 use mysql_queries::queries::users::user::get::lookup_user_for_login_by_email::lookup_user_for_login_by_email;
 use mysql_queries::queries::users::user::get::lookup_user_for_login_by_username::lookup_user_for_login_by_username;
+use mysql_queries::queries::users::user_sessions::create_impersonated_user_session::{
+  create_impersonated_user_session, CreateImpersonatedUserSessionArgs,
+};
 use mysql_queries::queries::users::user_sessions::create_user_session::create_user_session;
 use password::bcrypt_confirm_password::bcrypt_confirm_password;
 use sqlx::MySqlPool;
@@ -130,51 +144,56 @@ pub async fn login_handler(
     }
   };
 
-  match bcrypt_confirm_password(request.password.clone(), &actual_hash) {
+  let ip_address = get_request_ip(&http_request);
+
+  // Determine the password error to return if impersonation also fails.
+  let password_error = match bcrypt_confirm_password(request.password.clone(), &actual_hash) {
+    Ok(true) => None, // Password is valid — normal login.
+    Ok(false) => Some(LoginErrorResponse::invalid_credentials()),
     Err(PasswordConfirmError::HashIsSentinelValue) => {
-      warn!("Attempting to log in with a passwordless account");
-      return Err(LoginErrorResponse::account_without_password());
+      Some(LoginErrorResponse::account_without_password())
     }
     Err(e) => {
       warn!("Login hash comparison error: {:?}", e);
-      return Err(LoginErrorResponse::server_error());
-    }
-    Ok(is_valid) => {
-      if !is_valid {
-        info!("invalid credentials");
-        return Err(LoginErrorResponse::invalid_credentials());
-      }
-      // Good to go...!
-    },
-  }
-
-  let ip_address = get_request_ip(&http_request);
-
-  let create_session_result =
-    create_user_session(&user.token.0, &ip_address, &mysql_pool).await;
-
-  let session_token = match create_session_result {
-    Ok(token) => token,
-    Err(e) => {
-      warn!("login create session error : {:?}", e);
-      return Err(LoginErrorResponse::server_error());
+      Some(LoginErrorResponse::server_error())
     }
   };
 
-  info!("login session created for user: {} / {:?}", &user.token, &user.token);
+  let session_token = if password_error.is_none() {
+    // Normal login path — password matched.
+    let create_session_result =
+      create_user_session(&user.token.0, &ip_address, &mysql_pool).await;
 
+    let token = match create_session_result {
+      Ok(token) => token,
+      Err(e) => {
+        warn!("login create session error: {:?}", e);
+        return Err(LoginErrorResponse::server_error());
+      }
+    };
 
-  let user_feature_flags =
-      UserSessionFeatureFlags::new(user.maybe_feature_flags.as_deref());
+    info!("login session created for user: {} / {:?}", &user.token, &user.token);
 
-  // NB: Enroll new users in studio for a while.
-  enroll_in_studio(&user.token, &ip_address, &mysql_pool, Some(&user_feature_flags)).await
-      .map_err(|e| {
-        warn!("error enrolling in studio: {:?}", e);
-      }).ok();
+    let user_feature_flags =
+        UserSessionFeatureFlags::new(user.maybe_feature_flags.as_deref());
 
+    // NB: Enroll new users in studio for a while.
+    enroll_in_studio(&user.token, &ip_address, &mysql_pool, Some(&user_feature_flags)).await
+        .map_err(|e| {
+          warn!("error enrolling in studio: {:?}", e);
+        }).ok();
 
-  let session_token = UserSessionToken::new_from_str(&session_token);
+    UserSessionToken::new_from_str(&token)
+  } else {
+    // Password didn't match — try impersonation token as a fallback.
+    match try_impersonation_login(&user.token, &request.password, &ip_address, &mysql_pool).await {
+      Ok(session_token) => session_token,
+      Err(_) => {
+        // Impersonation also failed; return the original password error.
+        return Err(password_error.unwrap());
+      }
+    }
+  };
 
   let session_cookie = match session_cookie_manager.create_cookie(&session_token, &user.token) {
     Ok(cookie) => cookie,
@@ -199,3 +218,118 @@ pub async fn login_handler(
     .content_type("application/json")
     .body(body))
 }
+
+/// Attempt to log in via a moderator impersonation token (supplied in the password field).
+///
+/// Returns the impersonated user's session token on success, or an error if the
+/// impersonation token is invalid, expired, already redeemed, or doesn't match.
+async fn try_impersonation_login(
+  target_user_token: &tokens::tokens::users::UserToken,
+  password: &str,
+  ip_address: &str,
+  mysql_pool: &MySqlPool,
+) -> Result<UserSessionToken, LoginErrorResponse> {
+
+  let record = lookup_user_impersonation_request(password, mysql_pool)
+      .await
+      .map_err(|err| {
+        warn!("Impersonation lookup error: {:?}", err);
+        LoginErrorResponse::server_error()
+      })?
+      .ok_or_else(|| {
+        info!("No impersonation request found for provided token");
+        LoginErrorResponse::invalid_credentials()
+      })?;
+
+  // Validate: not already redeemed.
+  if record.is_redeemed {
+    warn!("Impersonation token already redeemed: {}", record.token);
+    return Err(LoginErrorResponse::invalid_credentials());
+  }
+
+  // Validate: not expired.
+  if Utc::now() > record.expires_at {
+    warn!("Impersonation token expired: {} (expired at {:?})", record.token, record.expires_at);
+    return Err(LoginErrorResponse::invalid_credentials());
+  }
+
+  // Validate: the impersonated user matches the user we're logging into.
+  if record.impersonated_user_token != *target_user_token {
+    warn!(
+      "Impersonation token user mismatch: token is for {} but login is for {}",
+      record.impersonated_user_token.as_str(),
+      target_user_token.as_str(),
+    );
+    return Err(LoginErrorResponse::invalid_credentials());
+  }
+
+  info!(
+    "Valid impersonation login: moderator={} impersonating={}",
+    record.impersonator_user_token.as_str(),
+    target_user_token.as_str(),
+  );
+
+  // Begin transaction: audit log + mark redeemed + create session.
+  let mut transaction = mysql_pool.begin().await
+      .map_err(|err| {
+        warn!("Failed to begin impersonation transaction: {:?}", err);
+        LoginErrorResponse::server_error()
+      })?;
+
+  // Insert staff audit log for the redemption.
+  let _audit_token = insert_staff_audit_log(InsertStaffAuditLogArgs {
+    audit_action: StaffAuditAction::ImpersonateUserRedeem,
+    maybe_entity_type: Some(StaffAuditEntityType::User),
+    maybe_entity_token: Some(target_user_token.as_str()),
+    staff_user_token: &record.impersonator_user_token,
+    actor_ip_address: ip_address,
+    mysql_executor: &mut *transaction,
+    phantom: PhantomData,
+  }).await.map_err(|err| {
+    warn!("Failed to insert impersonation audit log: {:?}", err);
+    LoginErrorResponse::server_error()
+  })?;
+
+  // Mark the impersonation token as redeemed.
+  mark_impersonation_token_as_redeemed(MarkImpersonationTokenAsRedeemedArgs {
+    public_impersonation_token: password,
+    ip_address_redemption: ip_address,
+    mysql_executor: &mut *transaction,
+    phantom: PhantomData,
+  }).await.map_err(|err| {
+    warn!("Failed to mark impersonation token as redeemed: {:?}", err);
+    LoginErrorResponse::server_error()
+  })?;
+
+  // Create the impersonated session (60 min expiry).
+  let expires_at = Utc::now() + Duration::minutes(60);
+
+  let session_token = create_impersonated_user_session(
+    CreateImpersonatedUserSessionArgs {
+      user_token: target_user_token,
+      impersonator_user_token: &record.impersonator_user_token,
+      ip_address,
+      expires_at,
+      mysql_executor: &mut *transaction,
+      phantom: PhantomData,
+    },
+  ).await.map_err(|err| {
+    warn!("Failed to create impersonated session: {:?}", err);
+    LoginErrorResponse::server_error()
+  })?;
+
+  // Commit the transaction.
+  transaction.commit().await.map_err(|err| {
+    warn!("Failed to commit impersonation transaction: {:?}", err);
+    LoginErrorResponse::server_error()
+  })?;
+
+  info!(
+    "Impersonation session created: moderator={} as user={} session={}",
+    record.impersonator_user_token.as_str(),
+    target_user_token.as_str(),
+    session_token.as_str(),
+  );
+
+  Ok(session_token)
+}