diff --git a/ElementX/Sources/Screens/RoomScreen/View/TimelineItemList.swift b/ElementX/Sources/Screens/RoomScreen/View/TimelineItemList.swift
index df7ddaacd..8ce2d45c9 100644
--- a/ElementX/Sources/Screens/RoomScreen/View/TimelineItemList.swift
+++ b/ElementX/Sources/Screens/RoomScreen/View/TimelineItemList.swift
@@ -82,20 +82,12 @@ struct TimelineItemList: View {
                     }
                 }
             }
-            .onChange(of: pinnedItem) { item in
-                guard let item else {
-                    return
-                }
-                
-                if item.animated {
-                    withAnimation(Animation.elementDefault) {
-                        proxy.scrollTo(item.id, anchor: item.anchor)
-                    }
-                } else {
-                    proxy.scrollTo(item.id, anchor: item.anchor)
-                }
-                
-                pinnedItem = nil
+            .onChange(of: timelineItems) { _ in
+                // Run this multiple times on first appearance to fix offset issues
+                updatePinnedOffset(scrollViewProxy: proxy)
+            }
+            .onChange(of: pinnedItem) { _ in
+                updatePinnedOffset(scrollViewProxy: proxy)
             }
         }
         .scrollDismissesKeyboard(.immediately)
@@ -148,8 +140,6 @@ struct TimelineItemList: View {
                 let pinnedItem = PinnedItem(id: currentFirstItem.id, anchor: .top, animated: false)
                 timelineItems = context.viewState.items
                 self.pinnedItem = pinnedItem
-                
-                return
             }
             
             // Otherwise just update the items
@@ -198,6 +188,25 @@ struct TimelineItemList: View {
         return selectedItemId == item.id ? 1.0 : 0.5
     }
     
+    private func updatePinnedOffset(scrollViewProxy proxy: ScrollViewProxy) {
+        guard let item = pinnedItem else {
+            return
+        }
+        
+        if item.animated {
+            withAnimation(.elementDefault) {
+                proxy.scrollTo(item.id, anchor: item.anchor)
+            }
+        } else {
+            proxy.scrollTo(item.id, anchor: item.anchor)
+        }
+        
+        // Need to delay this for a bit to fix offset problems when loading the initial page
+        DispatchQueue.main.asyncAfter(deadline: .now() + 0.1) {
+            pinnedItem = nil
+        }
+    }
+    
     private var isRunningPreviews: Bool {
         #if DEBUG
         return ProcessInfo.processInfo.environment["XCODE_RUNNING_FOR_PREVIEWS"] == "1"
diff --git a/changelog.d/pr-327.bugfix b/changelog.d/pr-327.bugfix
new file mode 100644
index 000000000..cbcf2d97e
--- /dev/null
+++ b/changelog.d/pr-327.bugfix
@@ -0,0 +1 @@
+Fixed timelines not sticking to the bottom on first appearance and when message heights change
\ No newline at end of file