diff --git a/src/module/feature/heroPointHandler/index.ts b/src/module/feature/heroPointHandler/index.ts
index 4036fab94..5fe304444 100644
--- a/src/module/feature/heroPointHandler/index.ts
+++ b/src/module/feature/heroPointHandler/index.ts
@@ -144,6 +144,42 @@ export async function heroPointHandler(state: HPHState) {
     handlerDialog.render(true);
 }
 
+// Constants
+const PARTY_MEMBERS_FLAG_KEY = "partymembersThatHaveGottenHeropoints";
+
+/**
+ * Selects a random party member index from the provided list of actors,
+ * ensuring the same actor is not repeatedly selected until all have been selected.
+ *
+ * @param {CreaturePF2e[]} actors - The list of party members to select from.
+ * @return {Promise<number>} The index of the selected actor in the input array, or -1 if the input array is empty.
+ */
+async function randomPartymemberThatHasNotReceivedAHeropoint(actors): Promise<number> {
+    if (actors.length === 0) {
+        await game.actors?.party?.unsetFlag(MODULENAME, PARTY_MEMBERS_FLAG_KEY);
+        return -1;
+    }
+
+    const existingFlagValue = String(game.actors?.party?.getFlag(MODULENAME, PARTY_MEMBERS_FLAG_KEY));
+    const hasReceivedHP: Set<string> = existingFlagValue ? new Set(existingFlagValue.split(",")) : new Set();
+    if (hasReceivedHP.size === actors.length) {
+        hasReceivedHP.clear();
+    }
+
+    const noHPYet = actors.filter((actor) => !hasReceivedHP.has(actor.id));
+    if (noHPYet.length === 0) {
+        hasReceivedHP.clear();
+        noHPYet.push(...actors);
+    }
+    const randomIndex: number = Math.floor(Math.random() * noHPYet.length);
+    const selectedActorId: string = noHPYet[randomIndex]?.id || actors[Math.floor(Math.random() * actors.length)]?.id;
+    hasReceivedHP.add(selectedActorId);
+
+    await game.actors?.party?.setFlag(MODULENAME, PARTY_MEMBERS_FLAG_KEY, [...hasReceivedHP].join(","));
+
+    return actors.findIndex((actor) => actor.id === selectedActorId);
+}
+
 async function buildHtml(remainingMinutes: number, state: HPHState) {
     // TODO How to start using bootstrap? (I use bootstrap classes in the html).
     // TODO Extract to a handlebars template
@@ -151,15 +187,25 @@ async function buildHtml(remainingMinutes: number, state: HPHState) {
     // TODO Get user name, add within parentheses after actor name
     let charactersContent = "";
     const actors = heroes();
-
     let checked: number;
     switch (state) {
         case HPHState.Start:
             checked = -1;
             break;
-        case HPHState.Timeout:
-            checked = actors.length > 0 ? Math.floor(Math.random() * actors.length) : -1;
+        case HPHState.Timeout: {
+            let selectedActor = -1;
+            switch (game.settings.get(MODULENAME, "heropointHandlerRandomization")) {
+                case "none":
+                    break;
+                case "random":
+                    selectedActor = Math.floor(Math.random() * actors.length);
+                    break;
+                case "randomPartymemberThatHasNotReceivedAHeropoint":
+                    selectedActor = await randomPartymemberThatHasNotReceivedAHeropoint(actors);
+            }
+            checked = actors.length > 0 ? selectedActor : -1;
             break;
+        }
         case HPHState.Check:
             checked = -1;
             break;
diff --git a/src/module/settings/reminders.ts b/src/module/settings/reminders.ts
index 3cf0bc99f..e56f913d1 100644
--- a/src/module/settings/reminders.ts
+++ b/src/module/settings/reminders.ts
@@ -132,6 +132,21 @@ export class WorkbenchRemindersSettings extends SettingsMenuPF2eWorkbench {
                 onChange: () => updateHooks(),
                 requiresReload: true,
             },
+            heropointHandlerRandomization: {
+                name: `${MODULENAME}.SETTINGS.heropointHandlerRandomization.name`,
+                hint: `${MODULENAME}.SETTINGS.heropointHandlerRandomization.hint`,
+                scope: "world",
+                config: true,
+                default: "random",
+                type: String,
+                choices: {
+                    none: game.i18n.localize(`${MODULENAME}.SETTINGS.heropointHandlerRandomization.none`),
+                    random: game.i18n.localize(`${MODULENAME}.SETTINGS.heropointHandlerRandomization.random`),
+                    randomPartymemberThatHasNotReceivedAHeropoint: game.i18n.localize(`${MODULENAME}.SETTINGS.heropointHandlerRandomization.randomPartymemberThatHasNotReceivedAHeropoint`),
+                },
+                onChange: () => updateHooks(),
+                requiresReload: true,
+            },
         };
     }
 }
diff --git a/static/lang/en.json b/static/lang/en.json
index 7d0f80dd1..578373715 100644
--- a/static/lang/en.json
+++ b/static/lang/en.json
@@ -482,6 +482,13 @@
         "hint": "Check to automatically start the Hero Point handler timer when the game is ready.",
         "name": "... and automatically start Hero Point Handler."
       },
+      "heropointHandlerRandomization": {
+        "hint": "How to select player to get random heropoint",
+        "name": "... how to select player to get random heropoint.",
+        "none": "No one",
+        "random": "A random partymember",
+        "randomPartymemberThatHasNotReceivedAHeropoint": "A partymember that hasn't gotten one yet."
+      },
       "housepatcher": {
         "hint": "(REALLY EXPERIMENTAL) Enter a json array to patch system compendiums. See housepatcher.md on the github for documentation.",
         "name": "(REALLY EXPERIMENTAL) Housepatcher (patches in house rules). Requires refresh (f5) after changing.",