diff --git a/modules/programs/zsh.nix b/modules/programs/zsh.nix
index f612aaaa..12d03645 100644
--- a/modules/programs/zsh.nix
+++ b/modules/programs/zsh.nix
@@ -190,18 +190,18 @@ let
     options = {
       enable = mkEnableOption "history substring search";
       searchUpKey = mkOption {
-        type = types.str;
-        default = "^[[A";
+        type = with types; either (listOf str) str ;
+        default = [ "^[[A" ];
         description = ''
-          The key code to be used when searching up.
+          The key codes to be used when searching up.
           The default of <literal>^[[A</literal> corresponds to the UP key.
         '';
       };
       searchDownKey = mkOption {
-        type = types.str;
-        default = "^[[B";
+        type = with types; either (listOf str) str ;
+        default = [ "^[[B" ];
         description = ''
-          The key code to be used when searching down.
+          The key codes to be used when searching down.
           The default of <literal>^[[B</literal> corresponds to the DOWN key.
         '';
       };
@@ -593,8 +593,14 @@ in
           # https://github.com/zsh-users/zsh-history-substring-search#usage
         ''
           source ${pkgs.zsh-history-substring-search}/share/zsh-history-substring-search/zsh-history-substring-search.zsh
-          bindkey '${cfg.historySubstringSearch.searchUpKey}' history-substring-search-up
-          bindkey '${cfg.historySubstringSearch.searchDownKey}' history-substring-search-down
+          ${lib.concatMapStringsSep "\n"
+            (upKey: "bindkey '${upKey}' history-substring-search-up")
+            (lib.toList cfg.historySubstringSearch.searchUpKey)
+          }
+          ${lib.concatMapStringsSep "\n"
+            (downKey: "bindkey '${downKey}' history-substring-search-down")
+            (lib.toList cfg.historySubstringSearch.searchDownKey)
+          }
         '')
       ]);
     }
diff --git a/tests/modules/programs/zsh/default.nix b/tests/modules/programs/zsh/default.nix
index 81e0d2d4..b9dc1b8c 100644
--- a/tests/modules/programs/zsh/default.nix
+++ b/tests/modules/programs/zsh/default.nix
@@ -5,5 +5,6 @@
   zsh-history-path-old-default = ./history-path-old-default.nix;
   zsh-history-path-old-custom = ./history-path-old-custom.nix;
   zsh-history-ignore-pattern = ./history-ignore-pattern.nix;
+  zsh-history-substring-search = ./history-substring-search.nix;
   zsh-prezto = ./prezto.nix;
 }
diff --git a/tests/modules/programs/zsh/history-substring-search.nix b/tests/modules/programs/zsh/history-substring-search.nix
new file mode 100644
index 00000000..4e9054d9
--- /dev/null
+++ b/tests/modules/programs/zsh/history-substring-search.nix
@@ -0,0 +1,25 @@
+{ config, lib, pkgs, ... }:
+
+with lib;
+
+{
+  config = {
+    programs.zsh = {
+      enable = true;
+      historySubstringSearch = {
+        enable = true;
+        searchDownKey = "^[[B";
+        searchUpKey = [ "^[[A" "\\eOA" ];
+      };
+    };
+
+    test.stubs.zsh = { };
+
+    # Written with regex to ensure we don't end up missing newlines in the future
+    nmt.script = ''
+      assertFileRegex home-files/.zshrc "^bindkey '\^\[\[B' history-substring-search-down$"
+      assertFileRegex home-files/.zshrc "^bindkey '\^\[\[A' history-substring-search-up$"
+      assertFileRegex home-files/.zshrc "^bindkey '\\\\eOA' history-substring-search-up$"
+    '';
+  };
+}