frontend/src/features/workspace/WorkspaceView.tsx

@@ -1081,7 +1081,8 @@ export const WorkspaceView: React.FC<WorkspaceViewProps> = ({
     afterIndex: number,
     level: number,
     type: BlockType = 'bullet',
-    initialContent: string = ''
+    initialContent: string = '',
+    updatedCurrentBlock?: { id: string; content: string }
   ) => {
     if (isReadOnly || !selectedDoc) return;
     const newBlock: DocumentBlock = {
@@ -1092,7 +1093,11 @@ export const WorkspaceView: React.FC<WorkspaceViewProps> = ({
       checked: false,
     };
 
-    const nextBlocks = [...selectedDoc.blocks];
+    const nextBlocks = selectedDoc.blocks.map((b) =>
+      updatedCurrentBlock && b.id === updatedCurrentBlock.id
+        ? { ...b, content: updatedCurrentBlock.content }
+        : b
+    );
     nextBlocks.splice(afterIndex + 1, 0, newBlock);
     persistDocument({ ...selectedDoc, blocks: nextBlocks });
     setLastFocusedBlockId(newBlock.id);
@@ -1247,7 +1252,7 @@ export const WorkspaceView: React.FC<WorkspaceViewProps> = ({
     }
   }, [activeEditingBlockId, activeCursorOffset, selectedDoc]);
 
-  // Keyboard Navigation: Enter, Tab, Shift+Tab, Backspace, / Slash Commands
+  // Keyboard Navigation: Enter, Shift+Enter, Tab, Shift+Tab, Backspace, / Slash Commands
   const handleKeyDown = (
     e: React.KeyboardEvent,
     block: DocumentBlock,
@@ -1290,22 +1295,57 @@ export const WorkspaceView: React.FC<WorkspaceViewProps> = ({
       }
     }
 
+    if (e.key === 'Enter' && e.shiftKey) {
+      // Shift+Enter: insert a newline within the current bullet point
+      if (block.type === 'bullet' || block.type === 'paragraph' || block.type === 'todo') {
+        e.preventDefault();
+        setSlashBlockId(null);
+        const target = e.target as HTMLTextAreaElement | HTMLInputElement;
+        const localPos =
+          target && typeof target.selectionStart === 'number'
+            ? target.selectionStart
+            : (target?.value || '').length;
+        const cursor = segStart + localPos;
+        const fullContent = block.content || '';
+        const nextContent = fullContent.slice(0, cursor) + '\n' + fullContent.slice(cursor);
+        const nextCursor = cursor + 1;
+        setBlockCursor(block.id, nextCursor);
+        updateBlock(block.id, { content: nextContent });
+      }
+      return;
+    }
+
     if (e.key === 'Enter' && !e.shiftKey) {
       e.preventDefault();
       setSlashBlockId(null);
       const target = e.target as HTMLTextAreaElement | HTMLInputElement;
-      let afterContent = '';
-      if (target && typeof target.selectionStart === 'number') {
-        const cursor = segStart + target.selectionStart;
       const fullContent = block.content || '';
+      let afterContent = '';
+      let updatedCurrent: { id: string; content: string } | undefined = undefined;
+
+      if (!fullContent.includes('\n') && target && typeof target.selectionStart === 'number') {
+        const cursor = segStart + target.selectionStart;
         const before = fullContent.slice(0, cursor);
         const after = fullContent.slice(cursor);
         if (after.length > 0) {
-          updateBlock(block.id, { content: before });
+          updatedCurrent = { id: block.id, content: before };
           afterContent = after;
         }
+      } else if (fullContent.endsWith('\n')) {
+        // Clean up trailing empty line if user pressed Shift+Enter then immediately Enter
+        const trimmedTrailing = fullContent.replace(/\n+$/, '');
+        if (trimmedTrailing !== fullContent) {
+          updatedCurrent = { id: block.id, content: trimmedTrailing };
         }
-      insertNewBulletAfter(index, block.level || 0, block.type === 'todo' ? 'todo' : 'bullet', afterContent);
+      }
+
+      insertNewBulletAfter(
+        index,
+        block.level || 0,
+        block.type === 'todo' ? 'todo' : 'bullet',
+        afterContent,
+        updatedCurrent
+      );
       return;
     } else if (e.key === 'Tab') {
       e.preventDefault();
@@ -1316,7 +1356,8 @@ export const WorkspaceView: React.FC<WorkspaceViewProps> = ({
       }
     } else if (e.key === 'Backspace') {
       const target = e.target as HTMLTextAreaElement | HTMLInputElement;
-      if (!block.content || block.content === '') {
+      const fullContent = block.content || '';
+      if (!fullContent || fullContent === '') {
         if ((block.level || 0) > 0) {
           e.preventDefault();
           outdentBlock(block.id);
@@ -1332,12 +1373,77 @@ export const WorkspaceView: React.FC<WorkspaceViewProps> = ({
         target.selectionEnd === 0
       ) {
         e.preventDefault();
-        setBlockCursor(block.id, segStart);
+        if (fullContent[segStart - 1] === '\n') {
+          // Join current line with previous line within the same bullet
+          const joined = fullContent.slice(0, segStart - 1) + fullContent.slice(segStart);
+          setBlockCursor(block.id, segStart - 1);
+          handleContentChange(block, joined);
+        } else {
+          // Move cursor into preceding inline token to unwrap it
+          setBlockCursor(block.id, segStart - 1);
         }
-    } else if (
+      }
-      !e.shiftKey &&
+    } else if (!e.shiftKey && e.key === 'ArrowLeft') {
-      (e.key === 'ArrowLeft' || e.key === 'ArrowRight' || e.key === 'Home' || e.key === 'End')
+      const target = e.target as HTMLTextAreaElement | HTMLInputElement;
+      if (segStart > 0 && target && target.selectionStart === 0 && target.selectionEnd === 0) {
+        e.preventDefault();
+        setBlockCursor(block.id, segStart - 1);
+        return;
+      }
+      requestAnimationFrame(() => {
+        if (target && typeof target.selectionStart === 'number') {
+          setBlockCursor(block.id, segStart + target.selectionStart);
+        }
+      });
+    } else if (!e.shiftKey && e.key === 'ArrowRight') {
+      const target = e.target as HTMLTextAreaElement | HTMLInputElement;
+      const fullContent = block.content || '';
+      if (
+        target &&
+        typeof target.selectionStart === 'number' &&
+        target.selectionStart === target.value.length &&
+        segStart + target.value.length < fullContent.length
       ) {
+        e.preventDefault();
+        setBlockCursor(block.id, segStart + target.value.length + 1);
+        return;
+      }
+      requestAnimationFrame(() => {
+        if (target && typeof target.selectionStart === 'number') {
+          setBlockCursor(block.id, segStart + target.selectionStart);
+        }
+      });
+    } else if (!e.shiftKey && (e.key === 'ArrowUp' || e.key === 'ArrowDown')) {
+      const target = e.target as HTMLTextAreaElement | HTMLInputElement;
+      const fullContent = block.content || '';
+      if (fullContent.includes('\n') && target && typeof target.selectionStart === 'number') {
+        const cursor = segStart + target.selectionStart;
+        const rawLines = fullContent.split('\n');
+        let run = 0;
+        const lineMeta = rawLines.map((lt) => {
+          const start = run;
+          const end = start + lt.length;
+          run = end + 1;
+          return { start, end, len: lt.length };
+        });
+        const curLineIdx = lineMeta.findIndex((m) => cursor >= m.start && cursor <= m.end);
+        if (curLineIdx !== -1) {
+          const col = cursor - lineMeta[curLineIdx].start;
+          if (e.key === 'ArrowUp' && curLineIdx > 0) {
+            e.preventDefault();
+            const prevLine = lineMeta[curLineIdx - 1];
+            setBlockCursor(block.id, prevLine.start + Math.min(col, prevLine.len));
+            return;
+          }
+          if (e.key === 'ArrowDown' && curLineIdx < lineMeta.length - 1) {
+            e.preventDefault();
+            const nextLine = lineMeta[curLineIdx + 1];
+            setBlockCursor(block.id, nextLine.start + Math.min(col, nextLine.len));
+            return;
+          }
+        }
+      }
+    } else if (!e.shiftKey && (e.key === 'Home' || e.key === 'End')) {
       const target = e.target as HTMLTextAreaElement | HTMLInputElement;
       requestAnimationFrame(() => {
         if (target && typeof target.selectionStart === 'number') {
@@ -1871,14 +1977,33 @@ export const WorkspaceView: React.FC<WorkspaceViewProps> = ({
     return <span key={key} className="whitespace-pre-wrap">{part}</span>;
   };
 
-  // Helper to render text with clickable Wiki-Links, Web-Links and Hashtags
+  // Helper to render text with clickable Wiki-Links, Web-Links and Hashtags across multiple lines
   const renderFormattedText = (text: string, blockId?: string) => {
-    const parts = text.split(/(\[\[.*?\]\]|\[.*?\]\(https?:\/\/[^\s)]+\)|#[a-zA-Z0-9äöüÄÖÜß_-]+)/g);
+    const rawLines = (text || '').split('\n');
+    if (rawLines.length <= 1) {
+      const parts = (text || '').split(/(\[\[.*?\]\]|\[.*?\]\(https?:\/\/[^\s)]+\)|#[a-zA-Z0-9äöüÄÖÜß_-]+)/g);
       return parts.map((part, i) => renderSingleRichToken(part, blockId, i));
+    }
+    return (
+      <div className="w-full space-y-0.5">
+        {rawLines.map((lineText, lineIdx) => {
+          const parts = lineText.split(/(\[\[.*?\]\]|\[.*?\]\(https?:\/\/[^\s)]+\)|#[a-zA-Z0-9äöüÄÖÜß_-]+)/g);
+          return (
+            <div key={lineIdx} className="flex flex-wrap items-center gap-y-0.5 w-full min-h-[22px]">
+              {lineText.length === 0 ? (
+                <span>&nbsp;</span>
+              ) : (
+                parts.map((part, i) => renderSingleRichToken(part, blockId, `${lineIdx}-${i}`))
+              )}
+            </div>
+          );
+        })}
+      </div>
+    );
   };
 
-  // Live inline token-aware editor: renders completed #hashtags and links inline as pills on the
+  // Live inline token-aware editor: splits multi-line bullets (Shift+Enter) into visual rows and renders
-  // exact same line while keeping any token currently touched by the cursor unwrapped as raw text.
+  // completed #hashtags and links inline as pills on each line while unwrapping any token touched by the cursor.
   const renderLiveInlineBlock = (
     block: DocumentBlock,
     originalIndex: number,
@@ -1893,32 +2018,90 @@ export const WorkspaceView: React.FC<WorkspaceViewProps> = ({
       );
     }
 
-    const allTokens = findRichTokens(text);
     const isEditing = activeEditingBlockId === block.id;
+    const cursor = isEditing ? Math.max(0, Math.min(text.length, activeCursorOffset)) : text.length;
 
-    if (!isEditing && allTokens.length > 0) {
+    const rawLines = text.split('\n');
-      const segments: (
+    let runningOffset = 0;
+    const lines = rawLines.map((lineText, lineIdx) => {
+      const lineStart = runningOffset;
+      const lineEnd = lineStart + lineText.length;
+      runningOffset = lineEnd + 1; // +1 for the '\n' delimiter
+      return { lineIdx, lineText, lineStart, lineEnd };
+    });
+
+    let activeLineIdx = lines.findIndex((l) => cursor >= l.lineStart && cursor <= l.lineEnd);
+    if (activeLineIdx === -1) {
+      activeLineIdx = lines.length - 1;
+    }
+
+    type InlineSegment =
       | { kind: 'text'; start: number; end: number; text: string }
-        | { kind: 'token'; start: number; end: number; raw: string }
+      | { kind: 'token'; start: number; end: number; raw: string };
-      )[] = [];
+
-      let lastIdx = 0;
+    return (
-      for (const t of allTokens) {
+      <div className={`w-full space-y-0.5 ${extraTextClass}`}>
+        {lines.map((line) => {
+          const isLineActive = isEditing && line.lineIdx === activeLineIdx;
+          const lineTokens = findRichTokens(line.lineText).map((t) => ({
+            start: line.lineStart + t.start,
+            end: line.lineStart + t.end,
+            raw: t.raw,
+          }));
+
+          // Non-active line (or block not currently focused)
+          if (!isLineActive) {
+            const segments: InlineSegment[] = [];
+            let lastIdx = line.lineStart;
+            for (const t of lineTokens) {
               if (t.start > lastIdx) {
-          segments.push({ kind: 'text', start: lastIdx, end: t.start, text: text.slice(lastIdx, t.start) });
+                segments.push({
+                  kind: 'text',
+                  start: lastIdx,
+                  end: t.start,
+                  text: text.slice(lastIdx, t.start),
+                });
               }
               segments.push({ kind: 'token', start: t.start, end: t.end, raw: t.raw });
               lastIdx = t.end;
             }
-      if (lastIdx < text.length) {
+            if (lastIdx < line.lineEnd) {
-        segments.push({ kind: 'text', start: lastIdx, end: text.length, text: text.slice(lastIdx) });
+              segments.push({
+                kind: 'text',
+                start: lastIdx,
+                end: line.lineEnd,
+                text: text.slice(lastIdx, line.lineEnd),
+              });
             }
 
             return (
               <div
-          onClick={() => focusBlock(block.id, text.length)}
+                key={`line-${line.lineIdx}`}
-          className={`flex flex-wrap items-center gap-y-0.5 w-full text-sm leading-relaxed break-words min-h-[22px] cursor-text ${extraTextClass}`}
+                onMouseDown={(e) => {
+                  if (e.target === e.currentTarget) {
+                    e.preventDefault();
+                    focusBlock(block.id, line.lineEnd);
+                  }
+                }}
+                onClick={(e) => {
+                  if (e.target === e.currentTarget) {
+                    focusBlock(block.id, line.lineEnd);
+                  }
+                }}
+                className="flex flex-wrap items-center gap-y-0.5 w-full text-sm leading-relaxed break-words min-h-[22px] cursor-text"
               >
-          {segments.map((seg, i) =>
+                {segments.length === 0 ? (
+                  <span
+                    onMouseDown={(e) => {
+                      e.preventDefault();
+                      focusBlock(block.id, line.lineStart);
+                    }}
+                    className="w-full min-h-[22px] inline-block"
+                  >
+                    &nbsp;
+                  </span>
+                ) : (
+                  segments.map((seg, i) =>
                     seg.kind === 'token' ? (
                       renderSingleRichToken(seg.raw, block.id, `tok-${seg.start}-${i}`)
                     ) : (
@@ -1938,22 +2121,16 @@ export const WorkspaceView: React.FC<WorkspaceViewProps> = ({
                         {seg.text}
                       </span>
                     )
+                  )
                 )}
               </div>
             );
           }
 
-    const cursor = isEditing ? Math.max(0, Math.min(text.length, activeCursorOffset)) : text.length;
+          // Active line being edited
-    const renderedTokens = isEditing
+          const renderedTokens = lineTokens.filter((t) => !(cursor >= t.start && cursor <= t.end));
-      ? allTokens.filter((t) => !(cursor >= t.start && cursor <= t.end))
-      : [];
-
-    type InlineSegment =
-      | { kind: 'text'; start: number; end: number; text: string }
-      | { kind: 'token'; start: number; end: number; raw: string };
-
           const segments: InlineSegment[] = [];
-    let lastIdx = 0;
+          let lastIdx = line.lineStart;
           for (const t of renderedTokens) {
             segments.push({
               kind: 'text',
@@ -1972,8 +2149,8 @@ export const WorkspaceView: React.FC<WorkspaceViewProps> = ({
           segments.push({
             kind: 'text',
             start: lastIdx,
-      end: text.length,
+            end: line.lineEnd,
-      text: text.slice(lastIdx),
+            text: text.slice(lastIdx, line.lineEnd),
           });
 
           let activeSegIdx = segments.findIndex(
@@ -1985,13 +2162,14 @@ export const WorkspaceView: React.FC<WorkspaceViewProps> = ({
 
           return (
             <div
+              key={`line-${line.lineIdx}`}
               onMouseDown={(e) => {
                 if (e.target === e.currentTarget) {
                   e.preventDefault();
-            focusBlock(block.id, text.length);
+                  focusBlock(block.id, line.lineEnd);
                 }
               }}
-        className={`flex flex-wrap items-center gap-y-0.5 w-full min-h-[22px] cursor-text ${extraTextClass}`}
+              className="flex flex-wrap items-center gap-y-0.5 w-full min-h-[22px] cursor-text"
             >
               {segments.map((seg, idx) => {
                 if (seg.kind === 'token') {
@@ -2066,6 +2244,9 @@ export const WorkspaceView: React.FC<WorkspaceViewProps> = ({
               })}
             </div>
           );
+        })}
+      </div>
+    );
   };
 
   // --- GLOBAL TO-DO ROLLUP AGGREGATOR ---
@@ -3120,7 +3301,7 @@ export const WorkspaceView: React.FC<WorkspaceViewProps> = ({
                           {/* TYPE: TODO */}
                           {block.type === 'todo' && (
                             <div className="space-y-1">
-                              <div className="flex items-center gap-2 group/todo">
+                              <div className="flex items-start gap-2 group/todo">
                                 <input
                                   type="checkbox"
                                   disabled={isReadOnly}
@@ -3134,7 +3315,7 @@ export const WorkspaceView: React.FC<WorkspaceViewProps> = ({
                                       onStatsChange();
                                     }
                                   }}
-                                  className={`w-4 h-4 checkbox-square flex-shrink-0 ${
+                                  className={`w-4 h-4 mt-1 checkbox-square flex-shrink-0 ${
                                     isReadOnly ? 'cursor-not-allowed opacity-60' : 'cursor-pointer'
                                   }`}
                                 />
@@ -3247,7 +3428,7 @@ export const WorkspaceView: React.FC<WorkspaceViewProps> = ({
                               <textarea
                                 ref={(el) => (blockInputRefs.current[block.id] = el)}
                                 readOnly={isReadOnly}
-                                rows={Math.max(1, Math.ceil((block.content || '').length / 70))}
+                                rows={Math.max(1, (block.content || '').split('\n').length, Math.ceil((block.content || '').length / 70))}
                                 value={block.content}
                                 onFocus={handleBlockFocus}
                                 onBlur={handleBlockBlur}

internal/storage/sqlite.go

@@ -1178,13 +1178,16 @@ func (s *Store) saveDocumentToDisk(doc *domain.Document) {
 				if b.Checked {
 					chk = "x"
 				}
-				md.WriteString(fmt.Sprintf("%s- [%s] %s\n", indent, chk, b.Content))
+				formatted := strings.ReplaceAll(b.Content, "\n", "\n"+indent+"  ")
+				md.WriteString(fmt.Sprintf("%s- [%s] %s\n", indent, chk, formatted))
 			case "bullet", "paragraph":
-				md.WriteString(fmt.Sprintf("%s- %s\n", indent, b.Content))
+				formatted := strings.ReplaceAll(b.Content, "\n", "\n"+indent+"  ")
+				md.WriteString(fmt.Sprintf("%s- %s\n", indent, formatted))
 			case "code":
 				md.WriteString(fmt.Sprintf("%s- ```%s\n%s  %s\n%s  ```\n", indent, b.Lang, indent, b.Content, indent))
 			case "callout":
-				md.WriteString(fmt.Sprintf("%s- > %s\n", indent, b.Content))
+				formatted := strings.ReplaceAll(b.Content, "\n", "\n"+indent+"  > ")
+				md.WriteString(fmt.Sprintf("%s- > %s\n", indent, formatted))
 			case "divider":
 				md.WriteString(fmt.Sprintf("%s- ---\n", indent))
 			case "table":
@@ -1192,7 +1195,8 @@ func (s *Store) saveDocumentToDisk(doc *domain.Document) {
 			case "progress":
 				md.WriteString(fmt.Sprintf("%s- <!-- progress: %s -->\n", indent, b.Content))
 			default:
-				md.WriteString(fmt.Sprintf("%s- %s\n", indent, b.Content))
+				formatted := strings.ReplaceAll(b.Content, "\n", "\n"+indent+"  ")
+				md.WriteString(fmt.Sprintf("%s- %s\n", indent, formatted))
 			}
 		}
 	} else if doc.Content != "" {