diff --git a/apps/dashboard/src/lib/features/course/api/newsfeed.svelte.ts b/apps/dashboard/src/lib/features/course/api/newsfeed.svelte.ts
index 74921360..d1e0ddf7 100644
--- a/apps/dashboard/src/lib/features/course/api/newsfeed.svelte.ts
+++ b/apps/dashboard/src/lib/features/course/api/newsfeed.svelte.ts
@@ -173,6 +173,7 @@ export class NewsfeedApi extends BaseApiWithErrors {
         ZNewsfeedUpdate.safeParse({ ...fields, content: '' }).error!,
         'newsfeed'
       );
+      snackbar.error(this.errors.content ?? 'Failed to update post');
       return;
     }
 
diff --git a/apps/dashboard/src/lib/features/course/components/newsfeed/card/card.svelte b/apps/dashboard/src/lib/features/course/components/newsfeed/card/card.svelte
index e56799cb..968b2a2f 100644
--- a/apps/dashboard/src/lib/features/course/components/newsfeed/card/card.svelte
+++ b/apps/dashboard/src/lib/features/course/components/newsfeed/card/card.svelte
@@ -1,5 +1,5 @@
 <script lang="ts">
-  import { onMount } from 'svelte';
+  import { onMount, tick } from 'svelte';
 
   import type { Feed } from '$features/course/utils/types';
   import { newsfeedApi } from '$features/course/api';
@@ -50,9 +50,10 @@
 
   let isDeleteFeedModal = $state(false);
 
-  const openEditFeed = () => {
+  const openEditFeed = async () => {
     editFeed = feed;
     edit = true;
+    await tick();
     newsfeedApi.openNewFeedModal();
   };
 
diff --git a/apps/dashboard/src/lib/features/course/components/newsfeed/new-feed-modal.svelte b/apps/dashboard/src/lib/features/course/components/newsfeed/new-feed-modal.svelte
index 583269eb..c9ce3209 100644
--- a/apps/dashboard/src/lib/features/course/components/newsfeed/new-feed-modal.svelte
+++ b/apps/dashboard/src/lib/features/course/components/newsfeed/new-feed-modal.svelte
@@ -17,21 +17,19 @@
   let { courseId = '', edit = $bindable(false), editFeed = $bindable() }: Props = $props();
 
   let isLoading = $state(false);
-  let errors: Record<string, string> = $state({
-    newPost: ''
-  });
-
   let newPost = $state('');
 
   $effect(() => {
     if (!newsfeedApi.isNewFeedModalOpen) {
-      newPost = '';
       return;
     }
 
     if (edit && editFeed) {
       newPost = editFeed.content || '';
+      return;
     }
+
+    newPost = '';
   });
 
   const onPost = async () => {
@@ -43,6 +41,10 @@
 
         if (newsfeedApi.success) {
           resetEditor();
+        } else if (newsfeedApi.errors.content) {
+          snackbar.error(newsfeedApi.errors.content);
+        } else {
+          snackbar.error('snackbar.newsfeed.error.editing');
         }
       } else {
         await newsfeedApi.create(courseId, {
@@ -101,8 +103,8 @@
           placeholder={$t('course.navItem.news_feed.heading_button.placeholder')}
         />
       {/key}
-      {#if errors.newPost}
-        <p class="text-sm text-red-500">{errors.newPost}</p>
+      {#if newsfeedApi.errors.content}
+        <p class="ui:text-destructive text-sm">{newsfeedApi.errors.content}</p>
       {/if}
     </section>
     <Dialog.Footer>
diff --git a/apps/dashboard/src/lib/features/program/components/newsfeed/card/card.svelte b/apps/dashboard/src/lib/features/program/components/newsfeed/card/card.svelte
index f27bbdde..0816962c 100644
--- a/apps/dashboard/src/lib/features/program/components/newsfeed/card/card.svelte
+++ b/apps/dashboard/src/lib/features/program/components/newsfeed/card/card.svelte
@@ -1,5 +1,5 @@
 <script lang="ts">
-  import { onMount } from 'svelte';
+  import { onMount, tick } from 'svelte';
   import type { ProgramNewsfeedItem } from '$features/program/utils/types';
   import { programNewsfeedApi, type ProgramNewsfeedCommentsByFeedId } from '$features/program/api';
   import {
@@ -59,10 +59,11 @@
   const reactionCounts = $derived(getNewsfeedReactionCounts(feed.reaction));
   const selectedReactionType = $derived(getSelectedNewsfeedReactionType(feed.reaction, reactionAuthorId));
 
-  const openEditFeed = () => {
-    programNewsfeedApi.openNewFeedModal();
-    edit = true;
+  const openEditFeed = async () => {
     editFeed = feed;
+    edit = true;
+    await tick();
+    programNewsfeedApi.openNewFeedModal();
   };
 
   const handleReact = (reactionType: string) => addNewReaction(reactionType, feed.id, reactionAuthorId);
diff --git a/apps/dashboard/src/lib/features/program/components/newsfeed/new-feed-modal.svelte b/apps/dashboard/src/lib/features/program/components/newsfeed/new-feed-modal.svelte
index 3be647ad..14554311 100644
--- a/apps/dashboard/src/lib/features/program/components/newsfeed/new-feed-modal.svelte
+++ b/apps/dashboard/src/lib/features/program/components/newsfeed/new-feed-modal.svelte
@@ -21,13 +21,15 @@
 
   $effect(() => {
     if (!programNewsfeedApi.isNewFeedModalOpen) {
-      newPost = '';
       return;
     }
 
     if (edit && editFeed) {
       newPost = editFeed.content || '';
+      return;
     }
+
+    newPost = '';
   });
 
   const resetEditor = () => {
diff --git a/packages/ui/add-ui-prefix.cjs b/packages/ui/add-ui-prefix.cjs
index fbf55eb2..af953ba1 100755
--- a/packages/ui/add-ui-prefix.cjs
+++ b/packages/ui/add-ui-prefix.cjs
@@ -28,6 +28,33 @@ const REPO_ROOT = path.join(__dirname, '../..');
 const UI_SRC_DIR = path.join(__dirname, 'src');
 const UI_SOURCE_EXTENSIONS = new Set(['.svelte', '.ts', '.tsx', '.js', '.jsx']);
 
+// Variant/prop literals — never Tailwind class strings (e.g. side === 'left', variant: 'outline')
+const SEMANTIC_LITERALS = new Set([
+  'left',
+  'right',
+  'top',
+  'bottom',
+  'center',
+  'start',
+  'end',
+  'outline',
+  'ghost',
+  'default',
+  'destructive',
+  'secondary',
+  'link',
+  'sm',
+  'md',
+  'lg',
+  'xl',
+  '2xl',
+  'icon',
+  'dot',
+  'line',
+  'page',
+  'none'
+]);
+
 // Collapse duplicate ui: markers (e.g. ui:hover:ui:bg-accent → ui:hover:bg-accent)
 function normalizeUiClass(className) {
   if (!className.includes(UI_PREFIX)) {
@@ -38,8 +65,36 @@ function normalizeUiClass(className) {
   return `${UI_PREFIX}${stripped}`;
 }
 
+function shouldProcessAsClassString(value) {
+  if (!value || value.trim() === '') {
+    return false;
+  }
+
+  if (SEMANTIC_LITERALS.has(value)) {
+    return false;
+  }
+
+  const tokens = value.split(/\s+/).filter(Boolean);
+  if (tokens.length === 0) {
+    return false;
+  }
+
+  if (tokens.some((token) => token.startsWith(UI_PREFIX))) {
+    return true;
+  }
+
+  const tailwindTokenCount = tokens.filter((token) => isTailwindClass(token)).length;
+
+  // Avoid treating prose in // comments (e.g. dialog's … sticky footer) as class strings.
+  return tailwindTokenCount >= Math.max(1, Math.ceil(tokens.length * 0.5));
+}
+
 // Check if a class looks like a Tailwind utility class
 function isTailwindClass(className) {
+  if (SEMANTIC_LITERALS.has(className)) {
+    return false;
+  }
+
   // Skip if already prefixed (including malformed mid-chain ui: after a variant)
   if (className.startsWith(UI_PREFIX) || className.includes(':ui:')) {
     return false;
@@ -156,8 +211,28 @@ function processClassString(classString, scopedClasses = new Set()) {
   return processClassTokens(classString, scopedClasses);
 }
 
+function repairCommentSwallowedClassStrings(content) {
+  // cn(..., // comment.'ui:classes', ...) — class string got glued into a line comment
+  return content.replace(
+    /^(\s*\/\/[^\n]*?)\.(['"]ui:[^'"]+['"],?\s*)$/gm,
+    (_, commentLine, classLiteral) => `${commentLine}.\n${classLiteral}`
+  );
+}
+
 function repairCorruptedQuotedPrefixes(content) {
-  return content.replace(/ui:'([^']*)'/g, "'ui:$1'").replace(/ui:"([^"]*)"/g, '"ui:$1"');
+  let repaired = content.replace(/ui:'([^']*)'/g, "'ui:$1'").replace(/ui:"([^"]*)"/g, '"ui:$1"');
+
+  for (const literal of SEMANTIC_LITERALS) {
+    const escaped = literal.replace(/[.*+?^${}()|[\]\\]/g, '\\$&');
+    repaired = repaired.replace(new RegExp(`===\\s*['"]${UI_PREFIX}${escaped}['"]`, 'g'), `=== '${literal}'`);
+    repaired = repaired.replace(new RegExp(`!==\\s*['"]${UI_PREFIX}${escaped}['"]`, 'g'), `!== '${literal}'`);
+    repaired = repaired.replace(
+      new RegExp(`(variant|side|align|size|indicator|density)\\s*:\\s*['"]${UI_PREFIX}${escaped}['"]`, 'g'),
+      `$1: '${literal}'`
+    );
+  }
+
+  return repaired;
 }
 
 function processInterpolatedSegments(value, scopedClasses, expressionPattern) {
@@ -191,11 +266,19 @@ function processQuotedClassStrings(content, scopedClasses = new Set()) {
   let processed = content;
 
   processed = processed.replace(/'([^']*)'/g, (match, quoted) => {
+    if (!shouldProcessAsClassString(quoted)) {
+      return match;
+    }
+
     const result = processClassString(quoted, scopedClasses);
     return result !== quoted ? `'${result}'` : match;
   });
 
   processed = processed.replace(/"([^"]*)"/g, (match, quoted) => {
+    if (!shouldProcessAsClassString(quoted)) {
+      return match;
+    }
+
     const result = processClassString(quoted, scopedClasses);
     return result !== quoted ? `"${result}"` : match;
   });
@@ -203,9 +286,22 @@ function processQuotedClassStrings(content, scopedClasses = new Set()) {
   return processed;
 }
 
+function processMultilineCnArgs(args, scopedClasses = new Set()) {
+  return args
+    .split('\n')
+    .map((line) => {
+      if (line.trimStart().startsWith('//')) {
+        return line;
+      }
+
+      return processQuotedClassStrings(line, scopedClasses);
+    })
+    .join('\n');
+}
+
 // Process file content
 function processFileContent(content, scopedClasses = new Set()) {
-  let modified = repairCorruptedQuotedPrefixes(content);
+  let modified = repairCommentSwallowedClassStrings(repairCorruptedQuotedPrefixes(content));
   let changes = modified !== content ? 1 : 0;
 
   // Helper to process and count changes
@@ -312,18 +408,30 @@ function processFileContent(content, scopedClasses = new Set()) {
 
     // Process double-quoted strings
     processedObj = processedObj.replace(/"([^"]*)"/g, (match, value) => {
+      if (!shouldProcessAsClassString(value)) {
+        return match;
+      }
+
       const processed = processClassString(value, scopedClasses);
       return processed !== value ? `"${processed}"` : match;
     });
 
     // Process single-quoted strings
     processedObj = processedObj.replace(/'([^']*)'/g, (match, value) => {
+      if (!shouldProcessAsClassString(value)) {
+        return match;
+      }
+
       const processed = processClassString(value, scopedClasses);
       return processed !== value ? `'${processed}'` : match;
     });
 
     // Process template literals
     processedObj = processedObj.replace(/`([^`]*)`/g, (match, value) => {
+      if (!shouldProcessAsClassString(value)) {
+        return match;
+      }
+
       const processed = processClassString(value, scopedClasses);
       return processed !== value ? `\`${processed}\`` : match;
     });
@@ -334,13 +442,13 @@ function processFileContent(content, scopedClasses = new Set()) {
   // Pattern 8: class: cn(...) patterns (like in derived props)
   // Matches: class: cn('string1', 'string2', ...)
   processAndReplace(/class:\s*cn\s*\(([^)]+)\)/g, (match, args) => {
-    const processedArgs = processQuotedClassStrings(args, scopedClasses);
+    const processedArgs = processMultilineCnArgs(args, scopedClasses);
     return processedArgs !== args ? `class: cn(${processedArgs})` : match;
   });
 
   // Pattern 8b: class={cn(...)} in Svelte markup (supports embedded quotes in class strings)
   processAndReplace(/class=\{cn\s*\(([\s\S]*?)\)\}/g, (match, args) => {
-    const processedArgs = processQuotedClassStrings(args, scopedClasses);
+    const processedArgs = processMultilineCnArgs(args, scopedClasses);
     return processedArgs !== args ? `class={cn(${processedArgs})}` : match;
   });
 
@@ -470,6 +578,17 @@ const AUDIT_PATTERNS = [
     id: 'inverted-variant-prefix',
     label: 'variant:ui:utility (ui: after variant instead of at start)',
     regex: /(?:^|[\s"'`{])(?:hover|focus|active|disabled|dark|sm|md|lg|xl|2xl|group-hover|peer-focus):ui:/
+  },
+  {
+    id: 'semantic-literal-prefix',
+    label: "Semantic prop/compare literals prefixed (e.g. === 'ui:left', side: 'ui:right')",
+    regex:
+      /===\s*['"]ui:(?:left|right|top|bottom|outline|ghost|default|center|start|end)['"]|(variant|side|align|size|indicator|density)\s*:\s*['"]ui:(?:left|right|top|bottom|outline|ghost|default)['"]/
+  },
+  {
+    id: 'comment-swallowed-class',
+    label: 'Class string glued into a // comment (dialog/chart cn() corruption)',
+    regex: /\/\/[^\n]*\.'ui:[^'\n]+'/
   }
 ];
 
diff --git a/packages/ui/src/base/chart/chart-container.svelte b/packages/ui/src/base/chart/chart-container.svelte
index 48e0c768..e492a48b 100644
--- a/packages/ui/src/base/chart/chart-container.svelte
+++ b/packages/ui/src/base/chart/chart-container.svelte
@@ -46,7 +46,12 @@
     // of the other series, this overrides that
     'ui:[&_.lc-area-path]:opacity-100 ui:[&_.lc-highlight-line]:opacity-100 ui:[&_.lc-highlight-point]:opacity-100 ui:[&_.lc-spline-path]:opacity-100 ui:[&_.lc-text]:text-xs ui:[&_.lc-text-svg]:overflow-visible',
 
-    // We don't want the little tick lines between the axis labels and the chart, so we remove // the stroke. The alternative is to manually disable `tickMarks` on the x/y axis of every // chart.'ui:[&_.lc-axis-tick]:stroke-0', // We don't want to display the rule on the x/y axis, as there is already going to be
+    // We don't want the little tick lines between the axis labels and the chart, so we remove
+    // the stroke. The alternative is to manually disable `tickMarks` on the x/y axis of every
+    // chart.
+    'ui:[&_.lc-axis-tick]:stroke-0',
+
+    // We don't want to display the rule on the x/y axis, as there is already going to be
     // a grid line there and rule ends up overlapping the marks because it is rendered after
     // the marks
     'ui:[&_.lc-rule-x-line:not(.lc-grid-x-rule)]:stroke-0 ui:[&_.lc-rule-y-line:not(.lc-grid-y-rule)]:stroke-0',
diff --git a/packages/ui/src/base/dialog/dialog-content.svelte b/packages/ui/src/base/dialog/dialog-content.svelte
index fe1d1476..8d81ab0c 100644
--- a/packages/ui/src/base/dialog/dialog-content.svelte
+++ b/packages/ui/src/base/dialog/dialog-content.svelte
@@ -26,8 +26,10 @@
     data-slot="dialog-content"
     class={cn(
       // `has-[[data-slot=dialog-footer][data-sticky=true]]:pb-0` drops the
-      // dialog's own ui:bottom padding when a ui:sticky footer is rendered — // the footer's own `py-4` provides the bottom spacing instead, and
-      // it pins flush with the dialog's ui:bottom edge.'ui:bg-background ui:border ui:data-[state=open]:animate-in ui:data-[state=closed]:animate-out ui:data-[state=closed]:fade-out-0 ui:data-[state=open]:fade-in-0 ui:data-[state=closed]:zoom-out-95 ui:data-[state=open]:zoom-in-95 ui:fixed ui:left-[50%] ui:top-[50%] ui:z-200 ui:grid ui:w-full ui:max-w-[calc(100%-2rem)] ui:translate-x-[-50%] ui:translate-y-[-50%] ui:gap-4 ui:rounded-lg ui:p-6 ui:[&:has([data-slot=dialog-footer][data-sticky=true])]:pb-0 ui:shadow-lg ui:duration-200 ui:sm:max-w-lg',
+      // dialog's own bottom padding when a sticky footer is rendered —
+      // the footer's own `py-4` provides the bottom spacing instead, and
+      // it pins flush with the dialog's bottom edge.
+      'ui:bg-background ui:border ui:data-[state=open]:animate-in ui:data-[state=closed]:animate-out ui:data-[state=closed]:fade-out-0 ui:data-[state=open]:fade-in-0 ui:data-[state=closed]:zoom-out-95 ui:data-[state=open]:zoom-in-95 ui:fixed ui:left-[50%] ui:top-[50%] ui:z-200 ui:grid ui:w-full ui:max-w-[calc(100%-2rem)] ui:translate-x-[-50%] ui:translate-y-[-50%] ui:gap-4 ui:rounded-lg ui:p-6 ui:[&:has([data-slot=dialog-footer][data-sticky=true])]:pb-0 ui:shadow-lg ui:duration-200 ui:sm:max-w-lg',
       className
     )}
     {...restProps}
diff --git a/packages/ui/src/base/pagination/pagination-link.svelte b/packages/ui/src/base/pagination/pagination-link.svelte
index f771c250..8f69c799 100644
--- a/packages/ui/src/base/pagination/pagination-link.svelte
+++ b/packages/ui/src/base/pagination/pagination-link.svelte
@@ -29,7 +29,7 @@
   data-active={isActive}
   class={cn(
     buttonVariants({
-      variant: isActive ? 'ui:outline' : 'ghost',
+      variant: isActive ? 'outline' : 'ghost',
       size
     }),
     className
diff --git a/packages/ui/src/base/sheet/sheet-content.svelte b/packages/ui/src/base/sheet/sheet-content.svelte
index ea6e8815..2a143a2b 100644
--- a/packages/ui/src/base/sheet/sheet-content.svelte
+++ b/packages/ui/src/base/sheet/sheet-content.svelte
@@ -13,7 +13,7 @@
       }
     },
     defaultVariants: {
-      side: 'ui:right'
+      side: 'right'
     }
   });
 
diff --git a/packages/ui/src/base/sidebar/sidebar.svelte b/packages/ui/src/base/sidebar/sidebar.svelte
index c46afcd8..389bfee2 100644
--- a/packages/ui/src/base/sidebar/sidebar.svelte
+++ b/packages/ui/src/base/sidebar/sidebar.svelte
@@ -78,7 +78,7 @@
       data-slot="sidebar-container"
       class={cn(
         'ui:w-(--sidebar-width) ui:fixed ui:inset-y-0 ui:z-100 ui:hidden ui:max-h-svh ui:transition-[left,right,width] ui:duration-200 ui:ease-linear ui:md:flex',
-        side === 'ui:left'
+        side === 'left'
           ? 'ui:left-0 ui:group-data-[collapsible=offcanvas]:left-[calc(var(--sidebar-width)*-1)]'
           : 'ui:right-0 ui:group-data-[collapsible=offcanvas]:right-[calc(var(--sidebar-width)*-1)]',
         // Adjust the padding for floating and inset variants.
diff --git a/packages/ui/src/custom/editor/ui/components/MediaExtended.svelte b/packages/ui/src/custom/editor/ui/components/MediaExtended.svelte
index 9493197e..c9a5a241 100644
--- a/packages/ui/src/custom/editor/ui/components/MediaExtended.svelte
+++ b/packages/ui/src/custom/editor/ui/components/MediaExtended.svelte
@@ -143,9 +143,9 @@
     class={cn(
       'ui:relative ui:my-2 ui:flex ui:flex-col ui:rounded-md ui:border-2 ui:border-transparent',
       selected ? 'ui:border-muted-foreground' : '',
-      node.attrs.align === 'ui:left' && 'ui:left-0 ui:-translate-x-0',
+      node.attrs.align === 'left' && 'ui:left-0 ui:-translate-x-0',
       node.attrs.align === 'center' && 'ui:left-1/2 ui:-translate-x-1/2',
-      node.attrs.align === 'ui:right' && 'ui:left-full ui:-translate-x-full'
+      node.attrs.align === 'right' && 'ui:left-full ui:-translate-x-full'
     )}
     style={`width: ${node.attrs.width}`}
   >
@@ -197,7 +197,7 @@
         >
           <Button
             variant="ghost"
-            class={cn('ui:size-6 ui:p-0', node.attrs.align === 'ui:left' && 'ui:bg-muted')}
+            class={cn('ui:size-6 ui:p-0', node.attrs.align === 'left' && 'ui:bg-muted')}
             onclick={() => updateAttributes({ align: 'left' })}
             title="Align Left"
           >
@@ -213,7 +213,7 @@
           </Button>
           <Button
             variant="ghost"
-            class={cn('ui:size-6 ui:p-0', node.attrs.align === 'ui:right' && 'ui:bg-muted')}
+            class={cn('ui:size-6 ui:p-0', node.attrs.align === 'right' && 'ui:bg-muted')}
             onclick={() => updateAttributes({ align: 'right' })}
             title="Align Right"
           >