diff --git a/CHANGELOG.md b/CHANGELOG.md
index 0659e9f98fc..2a5cf7658db 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -32,6 +32,7 @@ Docs: https://docs.openclaw.ai
 ### Fixes
 
 - Control UI/chat: show inline feedback when local slash-command dispatch is unavailable or fails unexpectedly instead of clearing the composer silently. Fixes #52105. Thanks @MooreQiao.
+- Memory/markdown: replace CRLF managed blocks in place and collapse duplicate marker blocks without rewriting unmanaged markdown, so Dreaming and Memory Wiki files self-heal from repeated generated sections. Fixes #75491; supersedes #75495, #75810, and #76008. Thanks @asaenokkostya-coder, @ottodeng, @everettjf, and @lrg913427-dot.
 - Agents/tools: return critical tool-loop circuit-breaker stops as blocked tool results instead of thrown tool failures, so models see the guardrail and stop retrying the same call. Thanks @rayraiser.
 - Model commands: clarify direct and inline `/model` acknowledgements for non-default selections as session-scoped. Thanks @addu2612.
 - TUI/chat: skip full provider model normalization during context-window warmup while preserving provider-owned context metadata, avoiding cold-start stalls with large model registries. Thanks @547895019.
diff --git a/src/plugin-sdk/memory-host-markdown.test.ts b/src/plugin-sdk/memory-host-markdown.test.ts
index 6bf4fc2eee5..c9a2884698f 100644
--- a/src/plugin-sdk/memory-host-markdown.test.ts
+++ b/src/plugin-sdk/memory-host-markdown.test.ts
@@ -47,4 +47,103 @@ describe("replaceManagedMarkdownBlock", () => {
       }),
     ).toBe("alpha\n\n<!-- start -->\nbeta\n<!-- end -->\n");
   });
+
+  it("replaces headed blocks with CRLF line endings in place", () => {
+    expect(
+      replaceManagedMarkdownBlock({
+        original: "# Title\r\n\r\n## Generated\r\n<!-- start -->\r\n- old\r\n<!-- end -->\r\n",
+        heading: "## Generated",
+        startMarker: "<!-- start -->",
+        endMarker: "<!-- end -->",
+        body: "- new",
+      }),
+    ).toBe("# Title\r\n\r\n## Generated\n<!-- start -->\n- new\n<!-- end -->\r\n");
+  });
+
+  it("collapses pre-existing duplicate managed blocks into one", () => {
+    const original = [
+      "# Title",
+      "",
+      "## Generated",
+      "<!-- start -->",
+      "- run-1",
+      "<!-- end -->",
+      "",
+      "## Generated",
+      "<!-- start -->",
+      "- run-2",
+      "<!-- end -->",
+      "",
+      "## Generated",
+      "<!-- start -->",
+      "- run-3",
+      "<!-- end -->",
+      "",
+    ].join("\n");
+
+    const updated = replaceManagedMarkdownBlock({
+      original,
+      heading: "## Generated",
+      startMarker: "<!-- start -->",
+      endMarker: "<!-- end -->",
+      body: "- latest",
+    });
+
+    expect(updated).toBe("# Title\n\n## Generated\n<!-- start -->\n- latest\n<!-- end -->\n");
+    expect(updated.match(/<!-- start -->/g)?.length).toBe(1);
+    expect(updated).not.toContain("run-");
+  });
+
+  it("preserves unmanaged markdown while removing duplicate blocks", () => {
+    const original = [
+      "# Title",
+      "",
+      "Paragraph A",
+      "",
+      "",
+      "Paragraph B",
+      "",
+      "## Generated",
+      "<!-- start -->",
+      "- old",
+      "<!-- end -->",
+      "",
+      "## Generated",
+      "<!-- start -->",
+      "- stale",
+      "<!-- end -->",
+      "",
+      "## Notes",
+      "kept",
+      "",
+      "",
+    ].join("\n");
+
+    expect(
+      replaceManagedMarkdownBlock({
+        original,
+        heading: "## Generated",
+        startMarker: "<!-- start -->",
+        endMarker: "<!-- end -->",
+        body: "- new",
+      }),
+    ).toBe(
+      "# Title\n\nParagraph A\n\n\nParagraph B\n\n## Generated\n<!-- start -->\n- new\n<!-- end -->\n\n## Notes\nkept\n\n",
+    );
+  });
+
+  it("is idempotent across repeated calls with the same body", () => {
+    const params = {
+      heading: "## Generated",
+      startMarker: "<!-- start -->",
+      endMarker: "<!-- end -->",
+      body: "- only",
+    } as const;
+    const first = replaceManagedMarkdownBlock({ original: "# Title\n", ...params });
+    const second = replaceManagedMarkdownBlock({ original: first, ...params });
+    const third = replaceManagedMarkdownBlock({ original: second, ...params });
+
+    expect(second).toBe(first);
+    expect(third).toBe(first);
+  });
 });
diff --git a/src/plugin-sdk/memory-host-markdown.ts b/src/plugin-sdk/memory-host-markdown.ts
index d9faf900989..d516cbc1c3d 100644
--- a/src/plugin-sdk/memory-host-markdown.ts
+++ b/src/plugin-sdk/memory-host-markdown.ts
@@ -10,6 +10,10 @@ function escapeRegex(value: string): string {
   return value.replace(/[.*+?^${}()|[\]\\]/g, "\\$&");
 }
 
+function isLineWhitespace(value: string): boolean {
+  return /^[\t \r\n]*$/.test(value);
+}
+
 export function withTrailingNewline(content: string): string {
   return content.endsWith("\n") ? content : `${content}\n`;
 }
@@ -17,13 +21,31 @@ export function withTrailingNewline(content: string): string {
 export function replaceManagedMarkdownBlock(params: ManagedMarkdownBlockParams): string {
   const headingPrefix = params.heading ? `${params.heading}\n` : "";
   const managedBlock = `${headingPrefix}${params.startMarker}\n${params.body}\n${params.endMarker}`;
+  const headingPattern = params.heading
+    ? `${escapeRegex(params.heading)}(?:[ \t]*(?:\r\n|\n|\r))+[ \t]*`
+    : "";
   const existingPattern = new RegExp(
-    `${params.heading ? `${escapeRegex(params.heading)}\\n` : ""}${escapeRegex(params.startMarker)}[\\s\\S]*?${escapeRegex(params.endMarker)}`,
-    "m",
+    `${headingPattern}${escapeRegex(params.startMarker)}[\\s\\S]*?${escapeRegex(params.endMarker)}`,
+    "g",
   );
+  const matches = Array.from(params.original.matchAll(existingPattern));
 
-  if (existingPattern.test(params.original)) {
-    return params.original.replace(existingPattern, managedBlock);
+  if (matches.length > 0) {
+    let updated = "";
+    let lastEnd = 0;
+    matches.forEach((match, index) => {
+      const matchStart = match.index ?? 0;
+      const matchEnd = matchStart + match[0].length;
+      const betweenMatches = params.original.slice(lastEnd, matchStart);
+      if (index === 0) {
+        updated += params.original.slice(0, matchStart);
+        updated += managedBlock;
+      } else if (!isLineWhitespace(betweenMatches)) {
+        updated += betweenMatches;
+      }
+      lastEnd = matchEnd;
+    });
+    return updated + params.original.slice(lastEnd);
   }
 
   const trimmed = params.original.trimEnd();