diff --git a/app/src/main/java/com/m57/hermescontrol/ui/chat/MarkdownText.kt b/app/src/main/java/com/m57/hermescontrol/ui/chat/MarkdownText.kt
index c2bdd24e..8f5de1c8 100644
--- a/app/src/main/java/com/m57/hermescontrol/ui/chat/MarkdownText.kt
+++ b/app/src/main/java/com/m57/hermescontrol/ui/chat/MarkdownText.kt
@@ -63,7 +63,7 @@ private val TABLE_COL_WIDTH = 160.dp
 private val FN_DEF_RE = Regex("""^\[\^([^\]]+)\]:\s*(.*)$""")
 private val BULLET_RE = Regex("""^\s*[-*+]\s+(.*)""")
 private val TASK_RE = Regex("""^\s*[-*+]\s+\[([ xX])\]\s+(.*)""")
-private val ORDERED_RE = Regex("""^\s*\d+\.\s+(.*)""")
+private val ORDERED_RE = Regex("""^\s*(\d+)\.\s+(.*)""")
 
 /**
  * Renders chat assistant text as Markdown — but ONLY once the message has finished streaming.
@@ -754,12 +754,25 @@ internal fun parseBlocks(src: String): List<MdBlock> {
             }
 
             ORDERED_RE.matches(line) -> {
-                val items = mutableListOf<String>()
-                while (i < lines.size && ORDERED_RE.matches(lines[i])) {
-                    items.add(ORDERED_RE.find(lines[i])!!.groupValues[1])
-                    i++
+                // Capture the source number so custom/loose lists keep their order.
+                // A blank line only breaks the list when the next non-blank line is NOT an
+                // ordered item — loose lists (blank lines between items) stay one list.
+                val items = mutableListOf<Pair<Int, String>>()
+                var j = i
+                while (j < lines.size) {
+                    val m = ORDERED_RE.find(lines[j])
+                    if (m != null) {
+                        val n = m.groupValues[1].toIntOrNull() ?: (items.size + 1)
+                        items.add(n to m.groupValues[2])
+                        j++
+                    } else if (lines[j].isBlank() && j + 1 < lines.size && ORDERED_RE.matches(lines[j + 1])) {
+                        j++
+                    } else {
+                        break
+                    }
                 }
-                items.forEachIndexed { idx, t -> blocks.add(MdBlock.Ordered(idx + 1, t)) }
+                items.forEach { (n, t) -> blocks.add(MdBlock.Ordered(n, t)) }
+                i = j
             }
 
             // Standalone Markdown image: ![alt](uri) on its own line.
diff --git a/app/src/test/java/com/m57/hermescontrol/ui/chat/MarkdownTextFeatureTest.kt b/app/src/test/java/com/m57/hermescontrol/ui/chat/MarkdownTextFeatureTest.kt
index 08745f49..636e7366 100644
--- a/app/src/test/java/com/m57/hermescontrol/ui/chat/MarkdownTextFeatureTest.kt
+++ b/app/src/test/java/com/m57/hermescontrol/ui/chat/MarkdownTextFeatureTest.kt
@@ -288,4 +288,51 @@ class MarkdownTextFeatureTest {
         assertTrue(videoAttachment.isVideo)
         assertFalse(videoAttachment.isImage)
     }
+
+    // 16. ORDERED LIST — loose lists must preserve numbering (issue #959)
+    @Test
+    fun testOrderedList_looseListPreservesNumbers() {
+        val md =
+            """
+            1. First
+
+            2. Second
+
+            3. Third
+            """.trimIndent()
+        val blocks = parseBlocks(md).filterIsInstance<MdBlock.Ordered>()
+        assertEquals(3, blocks.size)
+        assertEquals(1, blocks[0].index)
+        assertEquals(2, blocks[1].index)
+        assertEquals(3, blocks[2].index)
+        assertEquals("First", blocks[0].text)
+        assertEquals("Third", blocks[2].text)
+    }
+
+    // 16b. ORDERED LIST — custom starting number is preserved (issue #959)
+    @Test
+    fun testOrderedList_customStartNumberPreserved() {
+        val md =
+            """
+            2. Two
+            3. Three
+            """.trimIndent()
+        val blocks = parseBlocks(md).filterIsInstance<MdBlock.Ordered>()
+        assertEquals(2, blocks.size)
+        assertEquals(2, blocks[0].index)
+        assertEquals(3, blocks[1].index)
+    }
+
+    // 16c. ORDERED LIST — tight list still numbers sequentially
+    @Test
+    fun testOrderedList_tightList() {
+        val md =
+            """
+            1. one
+            2. two
+            3. three
+            """.trimIndent()
+        val blocks = parseBlocks(md).filterIsInstance<MdBlock.Ordered>()
+        assertEquals(listOf(1, 2, 3), blocks.map { it.index })
+    }
 }