diff --git a/src/components/InlineWikilinkParts.tsx b/src/components/InlineWikilinkParts.tsx
index d26a1802..7fe2a40e 100644
--- a/src/components/InlineWikilinkParts.tsx
+++ b/src/components/InlineWikilinkParts.tsx
@@ -176,6 +176,8 @@ export function InlineWikilinkEditorField({
   segments: InlineWikilinkSegment[]
   typeEntryMap: Record<string, VaultEntry>
 }) {
+  const needsTrailingCaretAnchor = segments[segments.length - 1]?.kind === 'chip'
+
   return (
     <div className="relative">
       {value.length === 0 && placeholder && (
@@ -218,6 +220,7 @@ export function InlineWikilinkEditorField({
                 />
               )
         ))}
+        {needsTrailingCaretAnchor ? '\u200B' : null}
       </div>
     </div>
   )
diff --git a/src/components/inlineWikilinkDom.ts b/src/components/inlineWikilinkDom.ts
index 08f4115f..f32c7773 100644
--- a/src/components/inlineWikilinkDom.ts
+++ b/src/components/inlineWikilinkDom.ts
@@ -68,7 +68,30 @@ export function readSelectionIndex(root: HTMLDivElement): number {
 }
 
 function boundaryAtEditorEnd(root: HTMLDivElement): SelectionBoundary {
-  return { container: root, offset: root.childNodes.length }
+  const endBoundary = findTextBoundaryAtEdge(root, 'end')
+  return endBoundary ?? { container: root, offset: root.childNodes.length }
+}
+
+function findTextBoundaryAtEdge(
+  node: Node,
+  edge: 'start' | 'end',
+): SelectionBoundary | null {
+  if (node.nodeType === Node.TEXT_NODE) {
+    return {
+      container: node,
+      offset: edge === 'start' ? 0 : node.textContent?.length ?? 0,
+    }
+  }
+
+  const children = Array.from(node.childNodes)
+  const orderedChildren = edge === 'start' ? children : children.toReversed()
+
+  for (const child of orderedChildren) {
+    const boundary = findTextBoundaryAtEdge(child, edge)
+    if (boundary) return boundary
+  }
+
+  return null
 }
 
 function boundaryForTextNode(
@@ -97,15 +120,21 @@ function boundaryForChip(
 ): { boundary: SelectionBoundary | null; remaining: number } {
   const tokenLength = chipToken(child.dataset.chipTarget ?? '').length
   if (remaining <= 0) {
+    const previousSibling = node.childNodes.item(index - 1)
     return {
-      boundary: { container: node, offset: index },
+      boundary: previousSibling
+        ? findTextBoundaryAtEdge(previousSibling, 'end') ?? { container: node, offset: index }
+        : { container: node, offset: index },
       remaining: 0,
     }
   }
 
   if (remaining <= tokenLength) {
+    const nextSibling = node.childNodes.item(index + 1)
     return {
-      boundary: { container: node, offset: index + 1 },
+      boundary: nextSibling
+        ? findTextBoundaryAtEdge(nextSibling, 'start') ?? { container: node, offset: index + 1 }
+        : { container: node, offset: index + 1 },
       remaining: 0,
     }
   }
diff --git a/tests/smoke/command-palette-ai-mode-regression.spec.ts b/tests/smoke/command-palette-ai-mode-regression.spec.ts
index c5c60711..b30e2999 100644
--- a/tests/smoke/command-palette-ai-mode-regression.spec.ts
+++ b/tests/smoke/command-palette-ai-mode-regression.spec.ts
@@ -1,4 +1,4 @@
-import { test, expect } from '@playwright/test'
+import { test, expect, type Page } from '@playwright/test'
 import { openCommandPalette } from './helpers'
 import {
   expectNoPageErrors,
@@ -7,6 +7,32 @@ import {
   trackPageErrors,
 } from './inlineWikilinkEditorHelpers'
 
+async function readCaretGapAfterChip(page: Page) {
+  return page.evaluate(() => {
+    const editor = document.querySelector('[data-testid="command-palette-ai-input"]')
+    if (!(editor instanceof HTMLElement)) return null
+
+    const chip = editor.querySelector('[data-testid="inline-wikilink-chip"]')
+    if (!(chip instanceof HTMLElement)) return null
+
+    const selection = window.getSelection()
+    if (selection === null) return null
+    if (selection.rangeCount === 0) return null
+
+    const range = selection.getRangeAt(0).cloneRange()
+    range.collapse(true)
+
+    const caretRect = range.getBoundingClientRect()
+    if (caretRect.height === 0) return null
+
+    return caretRect.left - chip.getBoundingClientRect().right
+  })
+}
+
+async function expectCaretAfterChip(page: Page) {
+  await expect.poll(() => readCaretGapAfterChip(page)).toBeLessThan(24)
+}
+
 test.describe('Command palette AI mode regression', () => {
   test.beforeEach(async ({ page }) => {
     await page.route('**/api/vault/ping', route => route.fulfill({ status: 503 }))
@@ -35,6 +61,7 @@ test.describe('Command palette AI mode regression', () => {
 
     await page.getByTestId('wikilink-menu').getByText('Build Laputa App').click()
     await expect(aiInput.getByTestId('inline-wikilink-chip')).toContainText('Build Laputa App')
+    await expectCaretAfterChip(page)
 
     await page.keyboard.type(' essay')
     await expectNormalizedEditorText(aiInput, 'edit my Build Laputa App essay')