diff --git a/src/HotKeyPanel.tsx b/src/HotKeyPanel.tsx
index fea02f6..5f4019f 100644
--- a/src/HotKeyPanel.tsx
+++ b/src/HotKeyPanel.tsx
@@ -3,12 +3,12 @@ import React, { useMemo, useState, useRef, useEffect } from "react";
 import MenuItemSelect from "roamjs-components/components/MenuItemSelect";
 import { getCleanCustomWorkflows } from "./utils/core";
 import type { OnloadArgs } from "roamjs-components/types/native";
+import { createAddHotKeyUpdater } from "./utils/createAddHotKeyUpdater";
 
 const HotKeyEntry = ({
   hotkey,
   value,
   order,
-  keys,
   setKeys,
   extensionAPI,
   workflows,
@@ -17,8 +17,7 @@ const HotKeyEntry = ({
   hotkey: string;
   value: string;
   order: number;
-  keys: Record<string, string>;
-  setKeys: (r: Record<string, string>) => void;
+  setKeys: React.Dispatch<React.SetStateAction<Record<string, string>>>;
   extensionAPI: OnloadArgs["extensionAPI"];
   workflows: { uid: string }[];
   workflowNamesByUid: Record<string, string>;
@@ -53,16 +52,21 @@ const HotKeyEntry = ({
                 : parts.concat(e.key.toLowerCase())
             ).join("+");
             if (formatValue === hotkey) return;
-            const error = !formatValue || !!keys[formatValue];
-            const newKeys = Object.fromEntries(
-              Object.entries(keys).map((k, o) =>
-                o !== order ? k : [formatValue, k[1]]
-              )
-            );
-            setKeys(newKeys);
-            if (!error) {
+            setKeys((currentKeys) => {
+              if (
+                !formatValue ||
+                (formatValue !== hotkey && !!currentKeys[formatValue])
+              ) {
+                return currentKeys;
+              }
+              const newKeys = Object.fromEntries(
+                Object.entries(currentKeys).map((k, o) =>
+                  o !== order ? k : [formatValue, k[1]]
+                )
+              );
               extensionAPI.settings.set("hot-keys", newKeys);
-            }
+              return newKeys;
+            });
           }}
           intent={Intent.NONE}
         />
@@ -73,11 +77,15 @@ const HotKeyEntry = ({
           activeItem={value}
           items={workflows.map((w) => w.uid)}
           onItemSelect={(e) => {
-            const newKeys = Object.fromEntries(
-              Object.entries(keys).map((k, o) => (o !== order ? k : [k[0], e]))
-            );
-            setKeys(newKeys);
-            extensionAPI.settings.set("hot-keys", newKeys);
+            setKeys((currentKeys) => {
+              const newKeys = Object.fromEntries(
+                Object.entries(currentKeys).map((k, o) =>
+                  o !== order ? k : [k[0], e]
+                )
+              );
+              extensionAPI.settings.set("hot-keys", newKeys);
+              return newKeys;
+            });
           }}
           transformItem={(e) => workflowNamesByUid[e]}
           className={"w-full"}
@@ -89,11 +97,13 @@ const HotKeyEntry = ({
         style={{ width: 32, height: 32 }}
         minimal
         onClick={() => {
-          const newKeys = Object.fromEntries(
-            Object.entries(keys).filter((_, o) => o !== order)
-          );
-          setKeys(newKeys);
-          extensionAPI.settings.set("hot-keys", newKeys);
+          setKeys((currentKeys) => {
+            const newKeys = Object.fromEntries(
+              Object.entries(currentKeys).filter((_, o) => o !== order)
+            );
+            extensionAPI.settings.set("hot-keys", newKeys);
+            return newKeys;
+          });
         }}
       />
     </div>
@@ -126,14 +136,13 @@ const HotKeyPanel = (extensionAPI: OnloadArgs["extensionAPI"]) => () => {
       {Object.entries(keys).map(([key, value], order) => {
         return (
           <HotKeyEntry
-            key={order}
+            key={`${key}-${order}`}
             hotkey={key}
             value={value}
             order={order}
             workflows={workflows}
             workflowNamesByUid={workflowNamesByUid}
             extensionAPI={extensionAPI}
-            keys={keys}
             setKeys={setKeys}
           />
         );
@@ -145,13 +154,16 @@ const HotKeyPanel = (extensionAPI: OnloadArgs["extensionAPI"]) => () => {
         minimal
         style={{ marginTop: 8 }}
         onClick={async () => {
+          if (!workflows.length) return;
           const randomWorkflow =
             workflows[Math.floor(Math.random() * workflows.length)];
-          const newKeys = Object.fromEntries(
-            Object.entries(keys).concat([["control+o", randomWorkflow.uid]])
+          setKeys(
+            createAddHotKeyUpdater({
+              randomWorkflowUid: randomWorkflow.uid,
+              setHotKeys: (newKeys) =>
+                extensionAPI.settings.set("hot-keys", newKeys),
+            })
           );
-          setKeys(newKeys);
-          extensionAPI.settings.set("hot-keys", newKeys);
         }}
       />
     </div>
diff --git a/src/utils/createAddHotKeyUpdater.ts b/src/utils/createAddHotKeyUpdater.ts
new file mode 100644
index 0000000..ab5555e
--- /dev/null
+++ b/src/utils/createAddHotKeyUpdater.ts
@@ -0,0 +1,21 @@
+import getNextAvailableHotKey from "./getNextAvailableHotKey";
+
+export const createAddHotKeyUpdater = ({
+  randomWorkflowUid,
+  setHotKeys,
+}: {
+  randomWorkflowUid: string;
+  setHotKeys: (keys: Record<string, string>) => void;
+}) =>
+  (currentKeys: Record<string, string>) => {
+    try {
+      const nextHotkey = getNextAvailableHotKey(currentKeys);
+      const newKeys = Object.fromEntries(
+        Object.entries(currentKeys).concat([[nextHotkey, randomWorkflowUid]])
+      );
+      setHotKeys(newKeys);
+      return newKeys;
+    } catch {
+      return currentKeys;
+    }
+  };
diff --git a/src/utils/getNextAvailableHotKey.ts b/src/utils/getNextAvailableHotKey.ts
new file mode 100644
index 0000000..a4d6505
--- /dev/null
+++ b/src/utils/getNextAvailableHotKey.ts
@@ -0,0 +1,21 @@
+const HOTKEY_MODIFIERS = ["control", "alt", "shift", "meta"];
+
+// Ordered by ergonomic preference: right-hand home row first (o, p, k, l),
+// then surrounding keys, then left hand, then digits.
+const HOTKEY_SUFFIXES = "opklijuyhgfdsawertqzxcvbnm1234567890".split("");
+
+const getNextAvailableHotKey = (keys: Record<string, string>) => {
+  for (const modifier of HOTKEY_MODIFIERS) {
+    for (const suffix of HOTKEY_SUFFIXES) {
+      const candidate = `${modifier}+${suffix}`;
+      if (!keys[candidate]) {
+        return candidate;
+      }
+    }
+  }
+  throw new Error(
+    "All hotkey combinations are in use. Remove an existing hotkey first."
+  );
+};
+
+export default getNextAvailableHotKey;
diff --git a/tests/hotKeyPanel.test.ts b/tests/hotKeyPanel.test.ts
new file mode 100644
index 0000000..df28ed8
--- /dev/null
+++ b/tests/hotKeyPanel.test.ts
@@ -0,0 +1,61 @@
+import { test, expect } from "@playwright/test";
+import { createAddHotKeyUpdater } from "../src/utils/createAddHotKeyUpdater";
+import getNextAvailableHotKey from "../src/utils/getNextAvailableHotKey";
+
+test("picks next control hotkey when control+o is taken", () => {
+  expect(getNextAvailableHotKey({ "control+o": "uid-1" })).toBe("control+p");
+});
+
+test("falls back to alt hotkeys when control combos are exhausted", () => {
+  const taken = Object.fromEntries(
+    "opklijuyhgfdsawertqzxcvbnm1234567890"
+      .split("")
+      .map((k, i) => [`control+${k}`, `uid-${i}`])
+  );
+  expect(getNextAvailableHotKey(taken)).toBe("alt+o");
+});
+
+test("throws when all modifier+suffix combos are exhausted", () => {
+  const allTaken: Record<string, string> = {};
+  for (const mod of ["control", "alt", "shift", "meta"]) {
+    for (const key of "opklijuyhgfdsawertqzxcvbnm1234567890".split("")) {
+      allTaken[`${mod}+${key}`] = `uid-${mod}-${key}`;
+    }
+  }
+  expect(() => getNextAvailableHotKey(allTaken)).toThrow();
+});
+
+test("createAddHotKeyUpdater adds next available hotkey and persists", () => {
+  const updates: Record<string, string>[] = [];
+  const updater = createAddHotKeyUpdater({
+    randomWorkflowUid: "uid-2",
+    setHotKeys: (keys) => updates.push(keys),
+  });
+
+  const result = updater({ "control+o": "uid-1" });
+
+  expect(result).toEqual({
+    "control+o": "uid-1",
+    "control+p": "uid-2",
+  });
+  expect(updates).toEqual([result]);
+});
+
+test("createAddHotKeyUpdater keeps state unchanged when combos exhausted", () => {
+  const updates: Record<string, string>[] = [];
+  const updater = createAddHotKeyUpdater({
+    randomWorkflowUid: "uid-next",
+    setHotKeys: (keys) => updates.push(keys),
+  });
+  const allTaken: Record<string, string> = {};
+  for (const mod of ["control", "alt", "shift", "meta"]) {
+    for (const key of "opklijuyhgfdsawertqzxcvbnm1234567890".split("")) {
+      allTaken[`${mod}+${key}`] = `uid-${mod}-${key}`;
+    }
+  }
+
+  const result = updater(allTaken);
+
+  expect(result).toBe(allTaken);
+  expect(updates).toEqual([]);
+});