diff --git a/src/plugins/fragment/index.js b/src/plugins/fragment/index.js
index d6f44e0..3c52991 100644
--- a/src/plugins/fragment/index.js
+++ b/src/plugins/fragment/index.js
@@ -1,14 +1,14 @@
 import { anchor_block } from "@/utilities/anchor_block";
 import { is_template, warn } from "@/utilities/utils";
 
-function plugin({ addScopeToNode, directive, initTree, mutateDom }) {
+function plugin({ addScopeToNode, directive, destroyTree, initTree, mutateDom }) {
     directive("fragment", (el, {}, { cleanup }) => {
         if (!is_template(el)) {
             warn("x-fragment can only be used on a 'template' tag");
             return;
         }
 
-        anchor_block(el, el, { addScopeToNode, cleanup, initTree, mutateDom });
+        anchor_block(el, el, { addScopeToNode, cleanup, destroyTree, initTree, mutateDom });
     });
 }
 
diff --git a/src/plugins/match/index.js b/src/plugins/match/index.js
index 16dc92e..43af1bf 100644
--- a/src/plugins/match/index.js
+++ b/src/plugins/match/index.js
@@ -2,7 +2,7 @@ import { anchor_block } from "@/utilities/anchor_block";
 import { create_getter } from "@/utilities/evaluator";
 import { is_template, warn } from "@/utilities/utils";
 
-function plugin({ addScopeToNode, directive, initTree, mutateDom }) {
+function plugin({ addScopeToNode, directive, destroyTree, initTree, mutateDom }) {
     directive("match", (el, { }, { cleanup, effect, evaluateLater }) => {
         if (!is_template(el)) {
             warn("x-match can only be used on a 'template' tag");
@@ -33,6 +33,7 @@ function plugin({ addScopeToNode, directive, initTree, mutateDom }) {
                 anchor_block(el, branch.el, {
                     addScopeToNode,
                     cleanup,
+                    destroyTree,
                     initTree,
                     mutateDom
                 });
diff --git a/src/plugins/when/index.js b/src/plugins/when/index.js
index f02f7a2..85dd890 100644
--- a/src/plugins/when/index.js
+++ b/src/plugins/when/index.js
@@ -2,14 +2,14 @@ import { anchor_block } from "@/utilities/anchor_block";
 import { create_getter } from "@/utilities/evaluator";
 import { is_template, warn } from "@/utilities/utils";
 
-function plugin({ addScopeToNode, directive, initTree, mutateDom }) {
+function plugin({ addScopeToNode, directive, destroyTree, initTree, mutateDom }) {
     directive("when", (el, { expression }, { cleanup, effect, evaluateLater }) => {
         if (!is_template(el)) {
             warn("x-when can only be used on a 'template' tag");
             return;
         }
 
-        const activate = () => anchor_block(el, el, { addScopeToNode, cleanup, initTree, mutateDom });
+        const activate = () => anchor_block(el, el, { addScopeToNode, cleanup, destroyTree, initTree, mutateDom });
         const clear = () => el._r_block?.delete();
 
         const get = create_getter(evaluateLater, expression);
diff --git a/src/utilities/anchor_block.js b/src/utilities/anchor_block.js
index 493c0a8..a194a7b 100644
--- a/src/utilities/anchor_block.js
+++ b/src/utilities/anchor_block.js
@@ -1,6 +1,6 @@
 import { is_element, is_template } from "@/utilities/utils";
 
-export function anchor_block(el, template, { addScopeToNode, cleanup, initTree, mutateDom, scope = {} }) {
+export function anchor_block(el, template, { addScopeToNode, cleanup, destroyTree, initTree, mutateDom, scope = {} }) {
     if (el._r_block) {
         return;
     }
@@ -30,9 +30,12 @@ export function anchor_block(el, template, { addScopeToNode, cleanup, initTree,
         },
         delete() {
             el._r_block = null;
-            for (let node of nodes ?? []) {
-                node.remove();
-            }
+            mutateDom(() => {
+                for (let node of nodes ?? []) {
+                    is_element(node) && destroyTree(node);
+                    node.remove();
+                }
+            });
             nodes = null;
         }
     }
diff --git a/tests/playwright/anchor-block.spec.js b/tests/playwright/anchor-block.spec.js
new file mode 100644
index 0000000..28d5f88
--- /dev/null
+++ b/tests/playwright/anchor-block.spec.js
@@ -0,0 +1,80 @@
+import { expect, test } from "@playwright/test";
+import { set_html } from "./assets/utils";
+
+for (const directive of ["fragment", "when", "match"]) {
+    test(`anchor block: nested cleanup (${directive})`, async ({ page }) => {
+        const errors = [];
+        page.on("pageerror", e => errors.push(e.message));
+
+        const content = `
+            Before
+            <dt x-data="{
+                destroy() {
+                    window.trace.destroy.push('dt')
+                }
+            }">Term</dt>
+            <template x-fragment>
+                <dd x-data="{ destroy() { window.trace.destroy.push('dd') } }"
+                    x-effect="window.trace.effects.push(tick)"
+                    @cleanup-probe.window="window.trace.events++">
+                    Description
+                </dd>
+                <!-- Nested comment -->
+                After
+            </template>`;
+
+        const block = directive === "match"
+            ? `<template id="block" x-match><template x-case="true">${content}</template></template>`
+            : `<template id="block" x-${directive}="true">${content}</template>`;
+
+        await set_html(page, `
+            <div x-data="{ tick: 0 }" id="app"
+                 x-init="window.trace = { destroy: [], effects: [], events: 0 }">
+                <dl id="content">${block}</dl>
+            </div>`);
+
+        await expect(page.locator("dt, dd")).toHaveText(["Term", "Description"]);
+
+        await page.evaluate(async () => {
+            Alpine.$data(document.querySelector("#app")).tick = 1;
+            window.dispatchEvent(new Event("cleanup-probe"));
+            await Alpine.nextTick();
+        });
+
+        expect(await page.evaluate(() => window.trace)).toEqual({
+            destroy: [],
+            effects: [0, 1],
+            events: 1
+        });
+
+        // Alpine 3.14.2+ cleans x-if/x-for clones with its observer disconnected
+        await page.evaluate(async () => {
+            const anchor = document.querySelector("#block");
+
+            Alpine.mutateDom(() => {
+                Alpine.destroyTree(anchor);
+                anchor.remove();
+            });
+
+            await Alpine.nextTick();
+        });
+
+        // Include text, comments and nested anchors, not just visible elements
+        expect(await page.locator("#content").evaluate(el => el.childNodes.length)).toBe(0);
+        expect(await page.evaluate(() => window.trace.destroy.toSorted())).toEqual(["dd", "dt"]);
+
+        await page.evaluate(async () => {
+            Alpine.$data(document.querySelector("#app")).tick = 2;
+            window.dispatchEvent(new Event("cleanup-probe"));
+            await Alpine.nextTick();
+        });
+
+        expect(await page.evaluate(() => ({ ...window.trace, destroy: window.trace.destroy.toSorted() }))).toEqual({
+            destroy: ["dd", "dt"],
+            effects: [0, 1],
+            events: 1
+        });
+
+        expect(errors).toEqual([]);
+    });
+}