diff --git a/src/api/ai_help.rs b/src/api/ai_help.rs
index 71f46625..0c97975b 100644
--- a/src/api/ai_help.rs
+++ b/src/api/ai_help.rs
@@ -22,9 +22,9 @@ use crate::{
     db::{
         self,
         ai_help::{
-            add_help_history, add_help_history_message, create_or_increment_total,
-            delete_full_help_history, delete_help_history, get_count, help_history,
-            help_history_get_message, list_help_history, update_help_history_label, AI_HELP_LIMIT,
+            add_help_history_message, create_or_increment_total, delete_full_help_history,
+            delete_help_history, get_count, help_history, help_history_get_message,
+            list_help_history, update_help_history_label, AI_HELP_LIMIT,
         },
         model::{AIHelpHistoryMessage, AIHelpHistoryMessageInsert, Settings},
         settings::get_settings,
@@ -207,9 +207,7 @@ fn record_question(
         message_id,
         parent_id,
     } = help_ids;
-    if let Err(err) = add_help_history(&mut conn, user_id, chat_id) {
-        error!("AI Help log: {err}");
-    }
+
     let insert = AIHelpHistoryMessageInsert {
         user_id,
         chat_id,
@@ -245,6 +243,7 @@ fn record_sources(
         message_id,
         parent_id,
     } = help_ids;
+
     let insert = AIHelpHistoryMessageInsert {
         user_id,
         chat_id,
diff --git a/src/db/ai_help.rs b/src/db/ai_help.rs
index 448442fc..e0ca699d 100644
--- a/src/db/ai_help.rs
+++ b/src/db/ai_help.rs
@@ -132,31 +132,63 @@ pub fn add_help_history(
         .do_update()
         .set(ai_help_history::updated_at.eq(diesel::dsl::now))
         .execute(conn)?;
-
     Ok(())
 }
 
-pub fn add_help_history_message(
+pub fn update_help_history(
     conn: &mut PgConnection,
-    mut message: AIHelpHistoryMessageInsert,
-) -> Result<NaiveDateTime, DbError> {
-    let updated_at = update(ai_help_history::table)
+    user_id: i64,
+    chat_id: Uuid,
+) -> Result<(), DbError> {
+    update(ai_help_history::table)
         .filter(
             ai_help_history::user_id
-                .eq(message.user_id)
-                .and(ai_help_history::chat_id.eq(message.chat_id)),
+                .eq(user_id)
+                .and(ai_help_history::chat_id.eq(chat_id)),
         )
         .set(ai_help_history::updated_at.eq(diesel::dsl::now))
-        .returning(ai_help_history::updated_at)
-        .get_result::<NaiveDateTime>(conn)?;
-    message.created_at = Some(updated_at);
-    insert_into(ai_help_history_messages::table)
+        .execute(conn)?;
+    Ok(())
+}
+
+pub fn add_help_history_message(
+    conn: &mut PgConnection,
+    message: AIHelpHistoryMessageInsert,
+) -> Result<NaiveDateTime, DbError> {
+    // If a `parent_id` is present, we execute an update on the help history
+    // record because one of these are true:
+    // * We created a history record at the beginning of the conversation.
+    // * History was switched off, we did not create a record and the update
+    //   will simply not match/change any record.
+    //
+    // With no `parent_id`, we create a new record because at this point, history
+    // _is_ enabled and we are at the start of a new conversation.
+    let res = if message.parent_id.is_some() {
+        update_help_history(conn, message.user_id, message.chat_id)
+    } else {
+        add_help_history(conn, message.user_id, message.chat_id)
+    };
+    if let Err(err) = res {
+        error!("AI Help log: {err}");
+    }
+
+    let res = insert_into(ai_help_history_messages::table)
         .values(&message)
         .on_conflict(ai_help_history_messages::message_id)
         .do_update()
         .set(&message)
-        .execute(conn)?;
-    Ok(updated_at)
+        .returning(ai_help_history_messages::created_at)
+        .get_result::<NaiveDateTime>(conn);
+    match res {
+        Ok(created_at) => Ok(created_at),
+        // Ignore foreign key violations deliberately
+        // because of the edge cases described above
+        Err(diesel::result::Error::DatabaseError(
+            diesel::result::DatabaseErrorKind::ForeignKeyViolation,
+            _info,
+        )) => Ok(Utc::now().naive_utc()),
+        Err(e) => Err(e.into()),
+    }
 }
 
 pub fn help_history_get_message(