diff --git a/app/assets/tailwind/sure-design-system/_generated.css b/app/assets/tailwind/sure-design-system/_generated.css
index 79ae54d43..355025e3b 100644
--- a/app/assets/tailwind/sure-design-system/_generated.css
+++ b/app/assets/tailwind/sure-design-system/_generated.css
@@ -25,7 +25,7 @@
   --color-container-inset: var(--color-gray-50);
   --color-container-inset-hover: var(--color-gray-100);
   --color-nav-indicator: var(--color-black);
-  --color-toggle-track: var(--color-gray-100);
+  --color-toggle-track: var(--color-gray-300);
   --color-destructive-subtle: var(--color-red-200);
   --color-gray-25: #FAFAFA;
   --color-gray-50: #F7F7F7;
@@ -294,7 +294,7 @@
   @apply text-gray-400;
 
   @variant theme-dark {
-    @apply text-gray-500;
+    @apply text-gray-400;
   }
 }
 
@@ -342,7 +342,7 @@
   @apply border-alpha-black-300;
 
   @variant theme-dark {
-    @apply border-alpha-white-400;
+    @apply border-alpha-white-500;
   }
 }
 
@@ -350,7 +350,7 @@
   @apply border-alpha-black-200;
 
   @variant theme-dark {
-    @apply border-alpha-white-300;
+    @apply border-alpha-white-400;
   }
 }
 
@@ -362,7 +362,7 @@
   @apply border-alpha-black-50;
 
   @variant theme-dark {
-    @apply border-alpha-white-100;
+    @apply border-alpha-white-200;
   }
 }
 
@@ -375,7 +375,7 @@
 }
 
 @utility border-destructive {
-  @apply border-red-500;
+  @apply border-red-600;
 
   @variant theme-dark {
     @apply border-red-400;
@@ -447,7 +447,7 @@
 }
 
 @utility button-bg-destructive {
-  @apply bg-red-500;
+  @apply bg-red-600;
 
   @variant theme-dark {
     @apply bg-red-400;
@@ -455,7 +455,7 @@
 }
 
 @utility button-bg-destructive-hover {
-  @apply bg-red-600;
+  @apply bg-red-700;
 
   @variant theme-dark {
     @apply bg-red-500;
diff --git a/app/assets/tailwind/sure-design-system/components.css b/app/assets/tailwind/sure-design-system/components.css
index 7d814388f..21a133c06 100644
--- a/app/assets/tailwind/sure-design-system/components.css
+++ b/app/assets/tailwind/sure-design-system/components.css
@@ -109,18 +109,27 @@
 
     @variant theme-dark {
       &[type='checkbox'] {
-        @apply ring-gray-900 checked:text-white;
-        background-color: var(--color-gray-100);
+        @apply ring-gray-900 border-alpha-white-300;
+        background-color: transparent;
       }
 
       &[type='checkbox']:disabled {
-        @apply cursor-not-allowed opacity-80;
-        background-color: var(--color-gray-600);
+        @apply cursor-not-allowed opacity-80 border-transparent;
+        background-color: var(--color-gray-700);
+      }
+
+      &[type='checkbox']:checked,
+      &[type='checkbox']:indeterminate {
+        @apply border-transparent;
+        background-color: var(--color-gray-100);
       }
 
       &[type='checkbox']:checked {
-        background-image: url("data:image/svg+xml,%3csvg viewBox='0 0 16 16' fill='%23808080' xmlns='http://www.w3.org/2000/svg'%3e%3cpath d='M12.207 4.793a1 1 0 010 1.414l-5 5a1 1 0 01-1.414 0l-2-2a1 1 0 011.414-1.414L6.5 9.086l4.293-4.293a1 1 0 011.414 0z'/%3e%3c/svg%3e");
-        background-color: var(--color-gray-100);
+        background-image: url("data:image/svg+xml,%3csvg viewBox='0 0 16 16' fill='%23171717' xmlns='http://www.w3.org/2000/svg'%3e%3cpath d='M12.207 4.793a1 1 0 010 1.414l-5 5a1 1 0 01-1.414 0l-2-2a1 1 0 011.414-1.414L6.5 9.086l4.293-4.293a1 1 0 011.414 0z'/%3e%3c/svg%3e");
+      }
+
+      &[type='checkbox']:indeterminate {
+        background-image: url("data:image/svg+xml,%3csvg viewBox='0 0 16 16' fill='%23171717' xmlns='http://www.w3.org/2000/svg'%3e%3crect x='3.5' y='7' width='9' height='2' rx='1'/%3e%3c/svg%3e");
       }
     }
   }
diff --git a/app/components/DS/buttonish.rb b/app/components/DS/buttonish.rb
index d7fa580a6..653151f95 100644
--- a/app/components/DS/buttonish.rb
+++ b/app/components/DS/buttonish.rb
@@ -9,7 +9,7 @@ class DS::Buttonish < DesignSystemComponent
       icon_classes: "text-primary"
     },
     destructive: {
-      container_classes: "text-inverse bg-red-500 theme-dark:bg-red-400 hover:bg-red-600 theme-dark:hover:bg-red-500 disabled:bg-red-200 theme-dark:disabled:bg-red-600",
+      container_classes: "text-inverse bg-red-600 theme-dark:bg-red-400 hover:bg-red-700 theme-dark:hover:bg-red-500 disabled:bg-red-200 theme-dark:disabled:bg-red-600",
       icon_classes: "text-inverse"
     },
     outline: {
diff --git a/app/components/DS/pill.rb b/app/components/DS/pill.rb
index b04ef61d6..c45bf056c 100644
--- a/app/components/DS/pill.rb
+++ b/app/components/DS/pill.rb
@@ -93,8 +93,13 @@ class DS::Pill < DesignSystemComponent
     p = palette
     case style
     when :filled
+      # Filled = solid / high-emphasis. The tone-500 fill fails white-label AA on
+      # the brighter tones (amber 2.4:1, green 2.6:1, red 4.0:1) and glares on dark
+      # surfaces. Deepen to tone-700 — every `fill` is a `*-500`, so derive -700 —
+      # so the white label clears AA on every tone in both themes.
+      strong_fill = p[:fill].sub("-500)", "-700)")
       <<~CSS.strip.gsub(/\s+/, " ")
-        background-color: #{p[:fill]};
+        background-color: #{strong_fill};
         color: var(--color-white);
         border-color: transparent;
       CSS
diff --git a/app/components/DS/toggle.rb b/app/components/DS/toggle.rb
index e45b69051..b1a47da4a 100644
--- a/app/components/DS/toggle.rb
+++ b/app/components/DS/toggle.rb
@@ -24,7 +24,7 @@ class DS::Toggle < DesignSystemComponent
        # `prefers-reduced-motion`; reduced-motion users get a snap.
        "motion-safe:transition-colors motion-safe:duration-300",
        "after:content-[''] after:block after:bg-white after:absolute after:rounded-full",
-       "after:top-0.5 after:left-0.5 after:w-4 after:h-4",
+       "after:top-0.5 after:left-0.5 after:w-4 after:h-4 after:shadow-sm",
        "motion-safe:after:transition-transform motion-safe:after:duration-300 motion-safe:after:ease-in-out",
        "peer-checked:bg-success peer-checked:after:translate-x-4",
        # Focus ring driven from the sr-only input via `peer-focus-visible:`.
diff --git a/app/views/budget_categories/_budget_category.html.erb b/app/views/budget_categories/_budget_category.html.erb
index 6b55b971e..647f2e91b 100644
--- a/app/views/budget_categories/_budget_category.html.erb
+++ b/app/views/budget_categories/_budget_category.html.erb
@@ -38,7 +38,7 @@
       <%# Progress Bar %>
       <div class="mb-3">
         <div class="h-1.5 bg-container-inset rounded-full overflow-hidden">
-          <% bar_color = budget_category.over_budget? ? "bg-red-500" : (budget_category.near_limit? ? "bg-yellow-500" : "bg-green-500") %>
+          <% bar_color = budget_category.over_budget? ? "bg-destructive" : (budget_category.near_limit? ? "bg-warning" : "bg-success") %>
           <div class="h-full <%= bar_color %> rounded-full transition-all duration-500"
             style="inline-size: <%= budget_category.bar_width_percent %>%"></div>
         </div>
@@ -67,8 +67,7 @@
           <div class="w-full sm:w-auto text-xs text-subdued">
             <%= t("reports.budget_performance.suggested_daily",
               amount: daily_info[:amount].format,
-              days: daily_info[:days_remaining])
-            %>
+              days: daily_info[:days_remaining]) %>
           </div>
         <% end %>
         <% end %>
diff --git a/design/tokens/sure.tokens.json b/design/tokens/sure.tokens.json
index bf36e8743..82b4a16fe 100644
--- a/design/tokens/sure.tokens.json
+++ b/design/tokens/sure.tokens.json
@@ -35,7 +35,7 @@
     "container-inset":       { "$value": "{color.gray.50}",          "$type": "color", "$extensions": { "sure.dark": "{color.gray.800}" } },
     "container-inset-hover": { "$value": "{color.gray.100}",         "$type": "color", "$extensions": { "sure.dark": "{color.gray.700}" } },
     "nav-indicator":         { "$value": "{color.black}",            "$type": "color", "$extensions": { "sure.dark": "{color.white}" } },
-    "toggle-track":          { "$value": "{color.gray.100}",         "$type": "color", "$extensions": { "sure.dark": "{color.gray.700}" } },
+    "toggle-track":          { "$value": "{color.gray.300}",         "$type": "color", "$extensions": { "sure.dark": "{color.gray.700}" } },
     "destructive-subtle":    { "$value": "{color.red.200}",          "$type": "color", "$extensions": { "sure.dark": "{color.red.800}" } },
 
     "gray": {
@@ -285,7 +285,7 @@
     "text-primary":   { "$type": "utility", "$value": "{color.gray.900}", "$extensions": { "sure.utility": { "prefix": "text" }, "sure.dark": "{color.white}" } },
     "text-inverse":   { "$type": "utility", "$value": "{color.white}",    "$extensions": { "sure.utility": { "prefix": "text" }, "sure.dark": "{color.gray.900}" } },
     "text-secondary": { "$type": "utility", "$value": "{color.gray.500}", "$extensions": { "sure.utility": { "prefix": "text" }, "sure.dark": "{color.gray.300}" } },
-    "text-subdued":   { "$type": "utility", "$value": "{color.gray.400}", "$extensions": { "sure.utility": { "prefix": "text" }, "sure.dark": "{color.gray.500}" } },
+    "text-subdued":   { "$type": "utility", "$value": "{color.gray.400}", "$extensions": { "sure.utility": { "prefix": "text" }, "sure.dark": "{color.gray.400}" } },
 
     "shadow-border-xs": {
       "$type": "utility",
@@ -328,12 +328,12 @@
       }
     },
 
-    "border-primary":     { "$type": "utility", "$value": "{color.alpha-black.300}", "$extensions": { "sure.utility": { "prefix": "border" }, "sure.dark": "{color.alpha-white.400}" } },
-    "border-secondary":   { "$type": "utility", "$value": "{color.alpha-black.200}", "$extensions": { "sure.utility": { "prefix": "border" }, "sure.dark": "{color.alpha-white.300}" } },
+    "border-primary":     { "$type": "utility", "$value": "{color.alpha-black.300}", "$extensions": { "sure.utility": { "prefix": "border" }, "sure.dark": "{color.alpha-white.500}" } },
+    "border-secondary":   { "$type": "utility", "$value": "{color.alpha-black.200}", "$extensions": { "sure.utility": { "prefix": "border" }, "sure.dark": "{color.alpha-white.400}" } },
     "border-divider":     { "$type": "utility", "$value": "border-tertiary" },
-    "border-subdued":     { "$type": "utility", "$value": "{color.alpha-black.50}",  "$extensions": { "sure.utility": { "prefix": "border" }, "sure.dark": "{color.alpha-white.100}" } },
+    "border-subdued":     { "$type": "utility", "$value": "{color.alpha-black.50}",  "$extensions": { "sure.utility": { "prefix": "border" }, "sure.dark": "{color.alpha-white.200}" } },
     "border-solid":       { "$type": "utility", "$value": "{color.black}",           "$extensions": { "sure.utility": { "prefix": "border" }, "sure.dark": "{color.white}" } },
-    "border-destructive": { "$type": "utility", "$value": "{color.red.500}",         "$extensions": { "sure.utility": { "prefix": "border" }, "sure.dark": "{color.red.400}" } },
+    "border-destructive": { "$type": "utility", "$value": "{color.red.600}",         "$extensions": { "sure.utility": { "prefix": "border" }, "sure.dark": "{color.red.400}" } },
     "border-inverse":     { "$type": "utility", "$value": "{color.alpha-white.200}", "$extensions": { "sure.utility": { "prefix": "border" }, "sure.dark": "{color.alpha-black.300}" } },
 
     "button-bg-primary":           { "$type": "utility", "$value": "{color.gray.900}", "$extensions": { "sure.utility": { "prefix": "bg" }, "sure.dark": "{color.white}" } },
@@ -343,8 +343,8 @@
     "button-bg-secondary-strong":       { "$type": "utility", "$value": "{color.gray.200}", "$extensions": { "sure.utility": { "prefix": "bg" }, "sure.dark": "{color.gray.700}" } },
     "button-bg-secondary-strong-hover": { "$type": "utility", "$value": "{color.gray.300}", "$extensions": { "sure.utility": { "prefix": "bg" }, "sure.dark": "{color.gray.600}" } },
     "button-bg-disabled":          { "$type": "utility", "$value": "{color.gray.50}",  "$extensions": { "sure.utility": { "prefix": "bg" }, "sure.dark": "{color.gray.700}" } },
-    "button-bg-destructive":       { "$type": "utility", "$value": "{color.red.500}",  "$extensions": { "sure.utility": { "prefix": "bg" }, "sure.dark": "{color.red.400}" } },
-    "button-bg-destructive-hover": { "$type": "utility", "$value": "{color.red.600}",  "$extensions": { "sure.utility": { "prefix": "bg" }, "sure.dark": "{color.red.500}" } },
+    "button-bg-destructive":       { "$type": "utility", "$value": "{color.red.600}",  "$extensions": { "sure.utility": { "prefix": "bg" }, "sure.dark": "{color.red.400}" } },
+    "button-bg-destructive-hover": { "$type": "utility", "$value": "{color.red.700}",  "$extensions": { "sure.utility": { "prefix": "bg" }, "sure.dark": "{color.red.500}" } },
     "button-bg-ghost-hover":       { "$type": "utility", "$value": "{color.gray.50}",  "$extensions": { "sure.utility": { "prefix": "bg" }, "sure.dark": "bg-gray-800 text-inverse" } },
     "button-bg-outline-hover":     { "$type": "utility", "$value": "{color.gray.100}", "$extensions": { "sure.utility": { "prefix": "bg" }, "sure.dark": "{color.gray.700}" } },