diff --git a/features/messages/impl/src/main/kotlin/io/element/android/features/messages/impl/timeline/components/event/TimelineItemImageView.kt b/features/messages/impl/src/main/kotlin/io/element/android/features/messages/impl/timeline/components/event/TimelineItemImageView.kt
index bef06bcd73..0e0a98a96c 100644
--- a/features/messages/impl/src/main/kotlin/io/element/android/features/messages/impl/timeline/components/event/TimelineItemImageView.kt
+++ b/features/messages/impl/src/main/kotlin/io/element/android/features/messages/impl/timeline/components/event/TimelineItemImageView.kt
@@ -58,6 +58,7 @@ import io.element.android.libraries.ui.utils.a11y.isTalkbackActive
 import io.element.android.wysiwyg.compose.EditorStyledText
 import io.element.android.wysiwyg.link.Link
 
+private const val TALL_IMAGE_RATIO_DIVISOR = 3
 @Composable
 fun TimelineItemImageView(
     content: TimelineItemImageContent,
@@ -79,7 +80,7 @@ fun TimelineItemImageView(
             Modifier
         }
         TimelineItemAspectRatioBox(
-            modifier = containerModifier.blurHashBackground(content.blurhash, alpha = 0.9f),
+            modifier = containerModifier.blurHashBackground(content.blurhash, alpha = 0.9f).align(Alignment.CenterHorizontally),
             aspectRatio = coerceRatioWhenHidingContent(content.aspectRatio, hideMediaContent),
         ) {
             ProtectedView(
@@ -123,7 +124,14 @@ fun TimelineItemImageView(
                 LocalContentColor provides ElementTheme.colors.textPrimary,
                 LocalTextStyle provides ElementTheme.typography.fontBodyLgRegular
             ) {
-                val aspectRatio = content.aspectRatio ?: DEFAULT_ASPECT_RATIO
+                val width = content.width ?: 0
+                val height = content.height ?: 0
+                // if image is narrow and tall use DEFAULT_ASPECT_RATIO
+                val aspectRatio = if (width < height / TALL_IMAGE_RATIO_DIVISOR) {
+                    DEFAULT_ASPECT_RATIO
+                } else {
+                    content.aspectRatio ?: DEFAULT_ASPECT_RATIO
+                }
                 EditorStyledText(
                     modifier = Modifier
                         .padding(horizontal = 4.dp) // This is (12.dp - 8.dp) contentPadding from CommonLayout
@@ -200,3 +208,38 @@ internal fun TimelineImageWithCaptionRowPreview() = ElementPreview {
         )
     }
 }
+
+@PreviewsDayNight
+@Composable
+internal fun ATimelineItemEventRowPreview() = ElementPreview {
+    Column {
+        sequenceOf(false, true).forEach { isMine ->
+            ATimelineItemEventRow(
+                event = aTimelineItemEvent(
+                    isMine = isMine,
+                    content = aTimelineItemImageContent(
+                        filename = "image.jpg",
+                        caption = "A long caption that may wrap into several lines",
+                        width = 80,
+                        height = 300,
+                        aspectRatio = 80f / 300f,
+                    ),
+                    groupPosition = TimelineItemGroupPosition.Last,
+                ),
+            )
+        }
+        ATimelineItemEventRow(
+            event = aTimelineItemEvent(
+                isMine = false,
+                content = aTimelineItemImageContent(
+                    filename = "image.jpg",
+                    caption = "Narrow image with null aspectRatio",
+                    width = 80,
+                    height = 300,
+                    aspectRatio = null,
+                ),
+                groupPosition = TimelineItemGroupPosition.Last,
+            ),
+        )
+    }
+}
diff --git a/features/messages/impl/src/main/kotlin/io/element/android/features/messages/impl/timeline/model/event/TimelineItemImageContentProvider.kt b/features/messages/impl/src/main/kotlin/io/element/android/features/messages/impl/timeline/model/event/TimelineItemImageContentProvider.kt
index d07d5db6a4..6d3b114428 100644
--- a/features/messages/impl/src/main/kotlin/io/element/android/features/messages/impl/timeline/model/event/TimelineItemImageContentProvider.kt
+++ b/features/messages/impl/src/main/kotlin/io/element/android/features/messages/impl/timeline/model/event/TimelineItemImageContentProvider.kt
@@ -28,6 +28,8 @@ fun aTimelineItemImageContent(
     blurhash: String? = A_BLUR_HASH,
     filename: String = "A picture.jpg",
     caption: String? = null,
+    width: Int? = null,
+    height: Int? = 300,
 ) = TimelineItemImageContent(
     filename = filename,
     fileSize = 4 * 1024 * 1024L,
@@ -38,8 +40,8 @@ fun aTimelineItemImageContent(
     thumbnailSource = null,
     mimeType = MimeTypes.IMAGE_JPEG,
     blurhash = blurhash,
-    width = null,
-    height = 300,
+    width = width,
+    height = height,
     thumbnailWidth = null,
     thumbnailHeight = 150,
     aspectRatio = aspectRatio,
diff --git a/libraries/androidutils/src/main/kotlin/io/element/android/libraries/androidutils/json/JsonProvider.kt b/libraries/androidutils/src/main/kotlin/io/element/android/libraries/androidutils/json/JsonProvider.kt
index 1e25599962..12f2957678 100644
--- a/libraries/androidutils/src/main/kotlin/io/element/android/libraries/androidutils/json/JsonProvider.kt
+++ b/libraries/androidutils/src/main/kotlin/io/element/android/libraries/androidutils/json/JsonProvider.kt
@@ -23,6 +23,13 @@ fun interface JsonProvider {
 @ContributesBinding(AppScope::class)
 @SingleIn(AppScope::class)
 class DefaultJsonProvider : JsonProvider {
-    private val json: Json by lazy { Json { ignoreUnknownKeys = true } }
+    private val json: Json by lazy {
+        Json {
+            ignoreUnknownKeys = true
+            allowComments = true
+            allowTrailingComma = true
+        }
+    }
+
     override fun invoke() = json
 }
diff --git a/libraries/wellknown/impl/src/test/kotlin/io/element/android/libraries/wellknown/impl/DefaultSessionWellknownRetrieverTest.kt b/libraries/wellknown/impl/src/test/kotlin/io/element/android/libraries/wellknown/impl/DefaultSessionWellknownRetrieverTest.kt
index faad139a36..e8c97c0220 100644
--- a/libraries/wellknown/impl/src/test/kotlin/io/element/android/libraries/wellknown/impl/DefaultSessionWellknownRetrieverTest.kt
+++ b/libraries/wellknown/impl/src/test/kotlin/io/element/android/libraries/wellknown/impl/DefaultSessionWellknownRetrieverTest.kt
@@ -80,7 +80,8 @@ class DefaultSessionWellknownRetrieverTest {
                     "registration_helper_url": "a_registration_url",
                     "enforce_element_pro": true,
                     "rageshake_url": "a_rageshake_url",
-                    "other": true
+                    // Note the trailing comma, and the comment!
+                    "other": true,
                 }""".trimIndent().toByteArray()
                 )
             },
diff --git a/tests/uitests/src/test/snapshots/images/features.messages.impl.timeline.components.event_ATimelineItemEventRow_Day_0_en.png b/tests/uitests/src/test/snapshots/images/features.messages.impl.timeline.components.event_ATimelineItemEventRow_Day_0_en.png
new file mode 100644
index 0000000000..08169845d5
--- /dev/null
+++ b/tests/uitests/src/test/snapshots/images/features.messages.impl.timeline.components.event_ATimelineItemEventRow_Day_0_en.png
@@ -0,0 +1,3 @@
+version https://git-lfs.github.com/spec/v1
+oid sha256:86eac241e9084cc830ff13d231908da2eb0dff246aa5cac64dddaac68a5d5f13
+size 295298
diff --git a/tests/uitests/src/test/snapshots/images/features.messages.impl.timeline.components.event_ATimelineItemEventRow_Night_0_en.png b/tests/uitests/src/test/snapshots/images/features.messages.impl.timeline.components.event_ATimelineItemEventRow_Night_0_en.png
new file mode 100644
index 0000000000..06dd93b269
--- /dev/null
+++ b/tests/uitests/src/test/snapshots/images/features.messages.impl.timeline.components.event_ATimelineItemEventRow_Night_0_en.png
@@ -0,0 +1,3 @@
+version https://git-lfs.github.com/spec/v1
+oid sha256:578a3707102c7754f607c3a14f94f32cafa30ee570db174386533c484cb4773c
+size 295031