diff --git a/modules/desktop/shells/dms/home-manager/default.nix b/modules/desktop/shells/dms/home-manager/default.nix
index c54399a..e708558 100644
--- a/modules/desktop/shells/dms/home-manager/default.nix
+++ b/modules/desktop/shells/dms/home-manager/default.nix
@@ -3,11 +3,36 @@
   config,
   pkgs,
   lib,
+  osConfig ? { },
   ...
 }: let
   home = config.home.homeDirectory;
   cfg = config.dms;
   gpuTempEnabled = cfg.enableGpuTemp;
+  hyprlandEnabled = lib.attrByPath [ "chiasson" "desktop" "hyprland" "enable" ] false osConfig;
+  discordEnabled = lib.attrByPath [ "chiasson" "home" "apps" "discord" "enable" ] false config;
+  ohMyPoshEnabled = config.programs.oh-my-posh.enable or false;
+  matugenOutputDirs =
+    lib.optionals hyprlandEnabled [ "${home}/.config/hypr" ]
+    ++ lib.optionals ohMyPoshEnabled [ "${home}/.config/oh-my-posh" ]
+    ++ lib.optionals discordEnabled [ "${home}/.config/vesktop/themes" ];
+  ensureMatugenOutputDirsScript = pkgs.writeShellScript "dms-ensure-matugen-output-dirs" ''
+    set -euo pipefail
+    ${lib.concatStringsSep "\n" (map (dir: "mkdir -p ${lib.escapeShellArg dir}") matugenOutputDirs)}
+    ${lib.optionalString ohMyPoshEnabled ''
+      dest="$HOME/.config/oh-my-posh/theme.omp.json"
+      template="$HOME/.config/matugen/templates/ohmyposh-theme.omp.json"
+      # matugen writes output_path in place; HM symlinks into the store are read-only and go stale.
+      if [ -L "$dest" ] || { [ -e "$dest" ] && ! [ -f "$dest" ]; }; then
+        rm -f "$dest"
+      fi
+      if [ ! -f "$dest" ]; then
+        # Seed from our matugen template (same generation closure), not programs.oh-my-posh.package
+        # which can reference a GC'd store path after profile churn.
+        cp -L "$template" "$dest"
+      fi
+    ''}
+  '';
   obsidianSnippetsDir = cfg.obsidianSnippetsDir; # legacy single path
   obsidianSnippetDirs =
     let
@@ -541,29 +566,40 @@ in {
     };
   };
 
+  # matugen won't create missing output_path parents; run before DMS theme generation.
+  systemd.user.services.dms.serviceConfig.ExecStartPre =
+    lib.mkOrder 100 "${ensureMatugenOutputDirsScript}";
+
   # DMS / matugen custom templates.
   #
   # DMS docs (custom templates): https://danklinux.com/docs/dankmaterialshell/application-themes#custom-matugen-templates
   xdg.configFile."matugen/config.toml".text =
     ''
     [config]
-
+    ''
+    + lib.optionalString hyprlandEnabled ''
     [templates.hyprland]
     input_path = '${home}/.config/matugen/templates/hyprland-colors.conf'
     output_path = '${home}/.config/hypr/colors.conf'
+    ''
+    + ''
 
     [templates.kdeglobals]
     input_path = '${home}/.config/matugen/templates/kdeglobals.conf'
     output_path = '${home}/.config/kdeglobals'
+    ''
+    + lib.optionalString ohMyPoshEnabled ''
 
     [templates.ohmyposh]
     input_path = '${home}/.config/matugen/templates/ohmyposh-theme.omp.json'
     output_path = '${home}/.config/oh-my-posh/theme.omp.json'
+    ''
+    + lib.optionalString discordEnabled ''
 
     [templates.dank-discord]
     input_path = '${home}/.config/matugen/templates/dank-discord.css'
     output_path = '${home}/.config/vesktop/themes/dank-discord.css'
-  ''
+    ''
     + lib.optionalString (obsidianSnippetDirs != []) (
       lib.concatStringsSep "\n" (
         lib.lists.imap0 (i: snippetDir: ''
@@ -576,6 +612,10 @@ in {
     )
     ;
 
+  home.activation.dmsEnsureMatugenOutputDirs = lib.hm.dag.entryAfter ["writeBoundary"] ''
+    ${ensureMatugenOutputDirsScript}
+  '';
+
   # Obsidian snippet dirs for matugen: mkdir here instead of tmpfiles (no chmod fights on weird mounts).
   home.activation.dmsEnsureObsidianSnippetDirs = lib.hm.dag.entryAfter ["writeBoundary"] (
     let
@@ -1107,14 +1147,8 @@ in {
     }
   '';
   }
-  (lib.mkIf (lib.attrByPath [ "chiasson" "home" "shell" "ohMyPosh" "enable" ] false config) {
-    # Matugen overwrites this at runtime; seed a stock theme so `oh-my-posh init fish` works before DMS runs matugen.
-    xdg.configFile."oh-my-posh/theme.omp.json".source =
-      let
-        ompTheme = config.chiasson.home.shell.ohMyPosh.builtinTheme or "jandedobbeleer";
-      in
-      "${config.programs.oh-my-posh.package}/themes/${ompTheme}.omp.json";
-    # Same path as matugen `[templates.ohmyposh]` output in `programs.dank-material-shell` config.
+  (lib.mkIf ohMyPoshEnabled {
+    # Same path as matugen `[templates.ohmyposh]`; seeded as a real file by `ensureMatugenOutputDirsScript`.
     programs.oh-my-posh = {
       useTheme = lib.mkForce null;
       configFile = lib.mkForce "${config.xdg.configHome}/oh-my-posh/theme.omp.json";