diff --git a/platforms/ios/lib/WysiwygComposer/Sources/WysiwygComposer/Components/WysiwygComposerView/WysiwygComposerViewModel.swift b/platforms/ios/lib/WysiwygComposer/Sources/WysiwygComposer/Components/WysiwygComposerView/WysiwygComposerViewModel.swift
index d0ae46d7b..8fb7b65da 100644
--- a/platforms/ios/lib/WysiwygComposer/Sources/WysiwygComposer/Components/WysiwygComposerView/WysiwygComposerViewModel.swift
+++ b/platforms/ios/lib/WysiwygComposer/Sources/WysiwygComposer/Components/WysiwygComposerView/WysiwygComposerViewModel.swift
@@ -121,7 +121,7 @@ public class WysiwygComposerViewModel: WysiwygComposerViewModelProtocol, Observa
          .foregroundColor: parserStyle.textColor]
     }
 
-    private var hasPendingFormats = false
+    private(set) var hasPendingFormats = false
 
     // MARK: - Public
 
@@ -183,8 +183,8 @@ public extension WysiwygComposerViewModel {
         let update = model.apply(action)
         if update.textUpdate() == .keep {
             hasPendingFormats = true
-        } else if action == .codeBlock || action == .quote, attributedContent.selection.length == 0 {
-            // Add code block/quote as a pending format to improve block display.
+        } else if attributedContent.selection.length == 0, action.requiresReapplyFormattingOnEmptySelection {
+            // Set pending format if current action requires it.
             hasPendingFormats = true
         }
         applyUpdate(update)
@@ -479,7 +479,12 @@ private extension WysiwygComposerViewModel {
         do {
             let htmlSelection = NSRange(location: Int(start), length: Int(end - start))
             let textSelection = try attributedContent.text.attributedRange(from: htmlSelection)
-            attributedContent.selection = textSelection
+            if textSelection != attributedContent.selection {
+                attributedContent.selection = textSelection
+                // Ensure we re-apply required pending formats when switching to a zero-length selection.
+                // This fixes selecting in and out of a list / quote / etc
+                hasPendingFormats = textSelection.length == 0 && !model.reversedActions.isEmpty
+            }
             Logger.viewModel.logDebug(["Sel(att): \(textSelection)",
                                        "Sel: \(htmlSelection)"],
                                       functionName: #function)
diff --git a/platforms/ios/lib/WysiwygComposer/Sources/WysiwygComposer/Extensions/ComposerAction.swift b/platforms/ios/lib/WysiwygComposer/Sources/WysiwygComposer/Extensions/ComposerAction.swift
new file mode 100644
index 000000000..03b1aeea0
--- /dev/null
+++ b/platforms/ios/lib/WysiwygComposer/Sources/WysiwygComposer/Extensions/ComposerAction.swift
@@ -0,0 +1,28 @@
+//
+// Copyright 2023 The Matrix.org Foundation C.I.C
+//
+// Licensed under the Apache License, Version 2.0 (the "License");
+// you may not use this file except in compliance with the License.
+// You may obtain a copy of the License at
+//
+// http://www.apache.org/licenses/LICENSE-2.0
+//
+// Unless required by applicable law or agreed to in writing, software
+// distributed under the License is distributed on an "AS IS" BASIS,
+// WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+// See the License for the specific language governing permissions and
+// limitations under the License.
+//
+
+extension ComposerAction {
+    /// Returns `true` if action requires all current formatting to be re-applied on
+    /// next character stroke when triggered on an empty selection.
+    var requiresReapplyFormattingOnEmptySelection: Bool {
+        switch self {
+        case .bold, .italic, .strikeThrough, .underline, .inlineCode, .link, .undo, .redo:
+            return false
+        case .orderedList, .unorderedList, .indent, .unindent, .codeBlock, .quote:
+            return true
+        }
+    }
+}
diff --git a/platforms/ios/lib/WysiwygComposer/Tests/WysiwygComposerTests/Components/WysiwygComposerView/WysiwygComposerViewModelTests.swift b/platforms/ios/lib/WysiwygComposer/Tests/WysiwygComposerTests/Components/WysiwygComposerView/WysiwygComposerViewModelTests.swift
index b8db2eed9..e61b54b5e 100644
--- a/platforms/ios/lib/WysiwygComposer/Tests/WysiwygComposerTests/Components/WysiwygComposerView/WysiwygComposerViewModelTests.swift
+++ b/platforms/ios/lib/WysiwygComposer/Tests/WysiwygComposerTests/Components/WysiwygComposerView/WysiwygComposerViewModelTests.swift
@@ -152,6 +152,37 @@ final class WysiwygComposerViewModelTests: XCTestCase {
                 .contains([.traitBold, .traitItalic])
         )
     }
+
+    func testPendingFormatFlagInNewList() {
+        viewModel.apply(.bold)
+        viewModel.apply(.italic)
+        mockTrailingTyping("Text")
+        viewModel.enter()
+        // After creating a list, pending format flag is on
+        viewModel.apply(.orderedList)
+        XCTAssertTrue(viewModel.hasPendingFormats)
+        // Typing consumes the flag
+        mockTrailingTyping("Item")
+        XCTAssertFalse(viewModel.hasPendingFormats)
+        // Creating a second list item re-enables the flag
+        viewModel.enter()
+        XCTAssertTrue(viewModel.hasPendingFormats)
+    }
+
+    func testPendingFormatFlagAfterReselectingListItem() {
+        viewModel.apply(.bold)
+        viewModel.apply(.italic)
+        mockTrailingTyping("Text")
+        viewModel.enter()
+        viewModel.apply(.orderedList)
+        let inListSelection = viewModel.attributedContent.selection
+        let insertedText = "Text"
+        mockTyping(insertedText, at: 0)
+        // After re-selecting the empty list item, pending format flag is still on
+        viewModel.select(range: NSRange(location: inListSelection.location + insertedText.utf16Length,
+                                        length: inListSelection.length))
+        XCTAssertTrue(viewModel.hasPendingFormats)
+    }
 }
 
 // MARK: - WysiwygTestExpectation
@@ -216,6 +247,7 @@ extension WysiwygComposerViewModelTests {
         if shouldAcceptChange {
             // Force apply since the text view should've updated by itself
             viewModel.textView.apply(viewModel.attributedContent)
+            viewModel.didUpdateText()
         }
     }
 
@@ -239,6 +271,7 @@ extension WysiwygComposerViewModelTests {
         if shouldAcceptChange {
             // Force apply since the text view should've updated by itself
             viewModel.textView.apply(viewModel.attributedContent)
+            viewModel.didUpdateText()
         }
     }