diff --git a/tools/server/public_simplechat/docs/changelog.md b/tools/server/public_simplechat/docs/changelog.md
index 747803d6bc..9d642de0a1 100644
--- a/tools/server/public_simplechat/docs/changelog.md
+++ b/tools/server/public_simplechat/docs/changelog.md
@@ -339,3 +339,10 @@ their respective functionalities.
 
 Add support for base64 encoded pdf passing to ai models, when the models and llama engine gain that capability
 in turn using openai file - file-data type sub block within content array or so ...
+
+See why the ai streamed response not showing up in TCExternalAi chat session ui, even thou the content is getting
+appended to its DivStream. IE why it is hidden.
+
+Markdown if a line which doesnt have any list marker appears at the same offset level as the last list item,
+that too after a new line before this ambiguous line, then maybe pop out 1 level wrt the list.
+
diff --git a/tools/server/public_simplechat/typemd.mjs b/tools/server/public_simplechat/typemd.mjs
index 2b07f417bf..da42938063 100644
--- a/tools/server/public_simplechat/typemd.mjs
+++ b/tools/server/public_simplechat/typemd.mjs
@@ -109,15 +109,23 @@ export class MarkDown {
         }
     }
 
-    unwind_list() {
-        while (true) {
+    /**
+     * Unwind till the specified offset level.
+     * @param {number} unwindTillOffset
+     */
+    unwind_list(unwindTillOffset=-1) {
+        if (this.in.list.offsets.length == 0) {
+            return { done: true, remaining: 0 }
+        }
+        while (this.in.list.offsets[this.in.list.offsets.length-1] > unwindTillOffset) {
+            this.in.list.offsets.pop()
             let popped = this.in.list.endType.pop()
-            if (popped == undefined) {
+            this.html += popped;
+            if (this.in.list.offsets.length == 0) {
                 break
             }
-            this.html += popped
         }
-        this.in.list.offsets.length = 0
+        return { done: true, remaining: this.in.list.offsets.length }
     }
 
     /**
@@ -154,20 +162,14 @@ export class MarkDown {
                     this.in.list.endType.push("</ul>\n")
                 }
             } else if (lastOffset > curOffset){
-                while (this.in.list.offsets[this.in.list.offsets.length-1] > curOffset) {
-                    this.in.list.offsets.pop()
-                    let popped = this.in.list.endType.pop()
-                    this.html += popped;
-                    if (this.in.list.offsets.length == 0) {
-                        break
-                    }
-                }
+                this.unwind_list(curOffset)
             }
             this.html += `<li>${matchList[3]}</li>\n`
             return true
         } else {
             if (this.in.list.offsets.length > 0) {
                 if (emptyTracker.cur > 0) {
+                    // skip empty line
                     return true
                 }
                 let matchOffset = line.match(/^([ ]*)(.*)$/);