diff --git a/core/home/config/nomarchy/default/mako/core.ini b/core/home/config/nomarchy/default/mako/core.ini
index 267f7cf..8d38674 100644
--- a/core/home/config/nomarchy/default/mako/core.ini
+++ b/core/home/config/nomarchy/default/mako/core.ini
@@ -22,12 +22,15 @@ layer=overlay
 
 [summary~="Setup Wi-Fi"]
 on-button-left=exec sh -c 'nomarchy-notification-dismiss "Setup Wi-Fi"; nomarchy-launch-wifi'
+on-click=exec sh -c 'nomarchy-notification-dismiss "Setup Wi-Fi"; nomarchy-launch-wifi'
 
 [summary~="Update System"]
 on-button-left=exec sh -c 'nomarchy-notification-dismiss "Update System"; nomarchy-launch-floating-terminal-with-presentation nomarchy-update'
+on-click=exec sh -c 'nomarchy-notification-dismiss "Update System"; nomarchy-launch-floating-terminal-with-presentation nomarchy-update'
 
 [summary~="Learn Keybindings"]
 on-button-left=exec sh -c 'nomarchy-notification-dismiss "Learn Keybindings"; nomarchy-menu-keybindings'
+on-click=exec sh -c 'nomarchy-notification-dismiss "Learn Keybindings"; nomarchy-menu-keybindings'
 
 [summary~="Screenshot copied & saved"]
 max-icon-size=80
diff --git a/core/system/default.nix b/core/system/default.nix
index 8cab932..9d2530e 100644
--- a/core/system/default.nix
+++ b/core/system/default.nix
@@ -18,6 +18,7 @@
     ./network.nix
     ./impermanence.nix
     ./browser.nix
+    ./file-manager.nix
     # Tier 1 system features (all opt-in via nomarchy.system.*).
     ./snapper.nix
     ./laptop.nix
diff --git a/core/system/file-manager.nix b/core/system/file-manager.nix
new file mode 100644
index 0000000..c4ff784
--- /dev/null
+++ b/core/system/file-manager.nix
@@ -0,0 +1,29 @@
+{ pkgs, lib, ... }:
+
+{
+  # Core system-side support for file management.
+  # This provides the backend services required by Thunar (and other file
+  # managers) to function correctly on a standalone compositor.
+
+  services.gvfs.enable = lib.mkDefault true;    # Mount, trash, and other file system operations
+  services.tumbler.enable = lib.mkDefault true; # Thumbnail support for images/videos/etc.
+
+  # Explicitly enable Thunar for D-Bus integration
+  programs.thunar.enable = lib.mkDefault true;
+
+  # Allow Thunar to use gvfs (trash, network mounts, etc.)
+  programs.thunar.plugins = with pkgs.xfce; [
+    thunar-archive-plugin
+    thunar-volman
+    thunar-media-tags-plugin
+  ];
+
+  # Supporting utilities for Thunar and general file management
+  environment.systemPackages = with pkgs; [
+    ffmpegthumbnailer # Video thumbnails
+    libgsf            # ODF thumbnails
+    poppler-utils     # PDF thumbnails
+    xfce.exo          # Required for "Open Terminal Here" and other associations
+    shared-mime-info  # Standard MIME database
+  ];
+}
diff --git a/docs/ROADMAP.md b/docs/ROADMAP.md
index a14282f..40ad1a3 100644
--- a/docs/ROADMAP.md
+++ b/docs/ROADMAP.md
@@ -19,12 +19,13 @@ Guardrails (apply when adding anything):
 
 ### Now (ready to pick up)
 
-_(empty — all entries shipped or moved to Later)_
+- **Deep Runtime Polish: App Integration.** Verify deeper NixOS integration for core apps in a live VM. Check **Thunar** (thumbnails, "Open Terminal Here"), **VSCode** (font propagation, extension loading), and **Mako** (clickable notification actions).
+- **Deep Runtime Polish: Interactive Script Audit (Round 2).** Run complex `nomarchy-*` commands inside a real Alacritty window in the VM. Identify and fix failures caused by TTY expectations, `$TERM` mismatches, or `gum` layout issues on specific themes.
+- **Deep Runtime Polish: State-Sync Stress Test.** Verify the robustness of the hybrid declarative state system (`nomarchy-state.nix`). Run automated "chaos" cycles (rapid theme/font/scaling changes) to catch race conditions or Nix generation errors.
+- **Deep Runtime Polish: Keybinding vs. Tooltip Reconciliation.** Ensure that `docs/KEYBINDINGS.md`, Waybar tooltips, and live Hyprland behavior are in perfect sync. Identify and fix stale references or conflicts with app-specific defaults.
 
 ### Next (bigger lifts that build on Now)
 
-_(empty — all entries shipped or moved to Later)_
-
 ### Later (speculative or research-shaped)
 
 - **Rolling vs pinned channel choice in the installer.**
diff --git a/features/scripts/utils/nomarchy-notification-dismiss b/features/scripts/utils/nomarchy-notification-dismiss
index 01e81da..edba138 100755
--- a/features/scripts/utils/nomarchy-notification-dismiss
+++ b/features/scripts/utils/nomarchy-notification-dismiss
@@ -9,8 +9,20 @@ if (($# == 0)); then
 fi
 
 # Find the first notification whose 'summary' matches the regex in $1
-notification_id=$(makoctl list | grep -F "$1" | head -n1 | sed -E 's/^Notification ([0-9]+):.*/\1/')
+output=$(makoctl list)
 
-if [[ -n $notification_id ]]; then
-  makoctl dismiss -n $notification_id
+if [[ $output == "["* ]] || [[ $output == "{"* ]]; then
+    # JSON format (mako 1.8+)
+    # Structure is usually an array of notifications or a wrapper object
+    notification_id=$(echo "$output" | jq -r --arg pat "$1" '
+        if type == "array" then . 
+        else .notifications // .data[0] // [] end
+        | .[] | select((.summary // .["summary-text"] // "") | contains($pat)) | .id' | head -n1)
+else
+    # Human format (older mako)
+    notification_id=$(echo "$output" | grep -F "$1" | head -n1 | sed -E 's/^Notification ([0-9]+):.*/\1/')
+fi
+
+if [[ "$notification_id" =~ ^[0-9]+$ ]]; then
+  makoctl dismiss -n "$notification_id"
 fi