diff --git a/packages/client/components/RetroReflectPhase/PhaseItemEditor.tsx b/packages/client/components/RetroReflectPhase/PhaseItemEditor.tsx
index f845732767d..6ab44e95a98 100644
--- a/packages/client/components/RetroReflectPhase/PhaseItemEditor.tsx
+++ b/packages/client/components/RetroReflectPhase/PhaseItemEditor.tsx
@@ -226,7 +226,7 @@ const PhaseItemEditor = (props: Props) => {
                 >
                   <div
                     className={cn(
-                      'ProseMirror flex max-h-28 min-h-4 w-full items-center px-4 pt-3 leading-none',
+                      'ProseMirror flex max-h-28 min-h-4 w-full flex-col items-start justify-center px-4 pt-3 leading-none',
                       disableAnonymity ? 'pb-0' : 'pb-3'
                     )}
                     dangerouslySetInnerHTML={{__html: card.html}}
diff --git a/packages/client/hooks/useBlockResizer.tsx b/packages/client/hooks/useBlockResizer.tsx
index d5383b98dcc..957b2e5087a 100644
--- a/packages/client/hooks/useBlockResizer.tsx
+++ b/packages/client/hooks/useBlockResizer.tsx
@@ -10,9 +10,9 @@ const makeDrag = () => ({
 })
 export const useBlockResizer = (
   width: number,
-  setWidth: (width: number) => void,
   updateAttributes: (attrs: Record<string, any>) => void,
-  aspectRatioRef: RefObject<number>
+  aspectRatioRef: RefObject<number>,
+  maxWidth: number
 ) => {
   const dragRef = useRef(makeDrag())
   const onMouseUp = useEventCallback((e: MouseEvent | TouchEvent) => {
@@ -41,8 +41,8 @@ export const useBlockResizer = (
     const sideCoefficient = drag.side === 'left' ? 1 : -1
     const delta = (drag.lastX - clientX) * sideCoefficient
     drag.lastX = clientX
-    const nextWidth = Math.max(48, width + delta)
-    setWidth(nextWidth)
+    const nextWidth = Math.min(maxWidth, Math.max(48, width + delta))
+    updateAttributes({width: nextWidth, height: Math.round(nextWidth / aspectRatioRef.current!)})
   })
 
   const onMouseDown = useEventCallback(
diff --git a/packages/client/hooks/useTipTapReflectionEditor.ts b/packages/client/hooks/useTipTapReflectionEditor.ts
index 9a493006083..7a644485328 100644
--- a/packages/client/hooks/useTipTapReflectionEditor.ts
+++ b/packages/client/hooks/useTipTapReflectionEditor.ts
@@ -70,7 +70,10 @@ export const useTipTapReflectionEditor = (
           'To-do list': false
         }),
         Focus,
-        ImageUpload.configure({editorWidth: ElementWidth.REFLECTION_CARD, editorHeight: 88}),
+        ImageUpload.configure({
+          editorWidth: ElementWidth.REFLECTION_CARD - 16 * 2,
+          editorHeight: 88
+        }),
         ImageBlock,
         LoomExtension,
         Placeholder.configure({
diff --git a/packages/client/tiptap/extensions/imageBlock/ImageBlock.ts b/packages/client/tiptap/extensions/imageBlock/ImageBlock.ts
index e574f6ee54d..e0e59746c79 100644
--- a/packages/client/tiptap/extensions/imageBlock/ImageBlock.ts
+++ b/packages/client/tiptap/extensions/imageBlock/ImageBlock.ts
@@ -13,14 +13,14 @@ export const ImageBlock = ImageBlockBase.extend({
         })
       },
       height: {
-        default: '100%',
+        default: undefined,
         parseHTML: (element) => element.getAttribute('height'),
         renderHTML: (attributes) => ({
           height: attributes.height
         })
       },
       width: {
-        default: '100%',
+        default: undefined,
         parseHTML: (element) => element.getAttribute('width'),
         renderHTML: (attributes) => ({
           width: attributes.width
diff --git a/packages/client/tiptap/extensions/imageBlock/ImageBlockView.tsx b/packages/client/tiptap/extensions/imageBlock/ImageBlockView.tsx
index 19295a9068c..014440f8d9e 100644
--- a/packages/client/tiptap/extensions/imageBlock/ImageBlockView.tsx
+++ b/packages/client/tiptap/extensions/imageBlock/ImageBlockView.tsx
@@ -1,5 +1,5 @@
 import {NodeViewWrapper, type NodeViewProps} from '@tiptap/react'
-import {useCallback, useEffect, useRef, useState} from 'react'
+import {useCallback, useRef, useState} from 'react'
 import {useBlockResizer} from '../../../hooks/useBlockResizer'
 import {cn} from '../../../ui/cn'
 import {BlockResizer} from './BlockResizer'
@@ -7,8 +7,8 @@ import {ImageBlockBubbleMenu} from './ImageBlockBubbleMenu'
 export const ImageBlockView = (props: NodeViewProps) => {
   const {editor, getPos, node, updateAttributes} = props
   const imageWrapperRef = useRef<HTMLDivElement>(null)
-  const {src, align} = node.attrs
-
+  const {attrs} = node
+  const {src, align, height, width} = attrs
   const alignClass =
     align === 'left' ? 'justify-start' : align === 'right' ? 'justify-end' : 'justify-center'
 
@@ -16,19 +16,20 @@ export const ImageBlockView = (props: NodeViewProps) => {
     editor.commands.setNodeSelection(getPos())
   }, [getPos, editor.commands])
 
-  const maxHeightRef = useRef<number | undefined>(editor.storage.imageUpload.editorHeight)
-  const {current: maxHeight} = maxHeightRef
-  const aspectRatioRef = useRef(0)
-  const ref = useRef<HTMLImageElement>(null)
-  const [width, setWidth] = useState<number>(node.attrs.width || 0)
-  const {onMouseDown} = useBlockResizer(width, setWidth, updateAttributes, aspectRatioRef)
+  const [maxHeight, setMaxHeight] = useState(
+    // if no height is provided (first load), make sure the image is no taller than the editor
+    height ? undefined : editor.storage.imageUpload.editorHeight
+  )
+
+  const aspectRatioRef = useRef(1)
+  const {onMouseDown} = useBlockResizer(
+    width,
+    updateAttributes,
+    aspectRatioRef,
+    editor.storage.imageUpload.editorWidth
+  )
   const onMouseDownLeft = onMouseDown('left')
   const onMouseDownRight = onMouseDown('right')
-  useEffect(() => {
-    if (width === node.attrs.width) return
-    // the attributes will change if another instance (e.g. a reflection in an expanded stack) edits them
-    setWidth(node.attrs.width)
-  }, [node.attrs.width])
   return (
     <NodeViewWrapper>
       <div className={cn('flex', alignClass)}>
@@ -38,15 +39,15 @@ export const ImageBlockView = (props: NodeViewProps) => {
             src={src}
             alt=''
             onClick={onClick}
-            style={{maxHeight, width: width === 0 ? undefined : width}}
-            ref={ref}
+            style={{maxHeight}}
+            width={width}
+            height={height}
             onLoad={(e) => {
               const img = e.target as HTMLImageElement
-              console.log('loaded', img.width, img.height, maxHeightRef.current)
-              maxHeightRef.current = undefined
               aspectRatioRef.current = img.width / img.height
-              if (img.width !== node.attrs.width) {
-                setWidth(img.width)
+              if (img.width !== width) {
+                // on initial load, once we grab the h/w/ar, remove the maxH constraint
+                setMaxHeight(undefined)
                 updateAttributes({width: img.width, height: img.height})
               }
             }}