diff --git a/editor/src/components/canvas/plugins/tailwind-style-plugin-utils/tailwind-responsive-utils.ts b/editor/src/components/canvas/plugins/tailwind-style-plugin-utils/tailwind-responsive-utils.ts
index 6782d6fee6a0..f77ed1584e51 100644
--- a/editor/src/components/canvas/plugins/tailwind-style-plugin-utils/tailwind-responsive-utils.ts
+++ b/editor/src/components/canvas/plugins/tailwind-style-plugin-utils/tailwind-responsive-utils.ts
@@ -1,8 +1,11 @@
 import type { Config } from 'tailwindcss/types/config'
-import { type StyleMediaSizeModifier, type StyleModifier } from '../../canvas-types'
+import { isStyleInfoKey, type StyleMediaSizeModifier, type StyleModifier } from '../../canvas-types'
 import type { ScreenSize } from '../../responsive-types'
 import { extractScreenSizeFromCss } from '../../responsive-utils'
 import { mapDropNulls } from '../../../../core/shared/array-utils'
+import { getTailwindClassMapping, TailwindPropertyMapping } from '../tailwind-style-plugin'
+import { parseTailwindPropertyFactory } from '../tailwind-style-plugin'
+import type { StylePluginContext } from '../style-plugins'
 
 export const TAILWIND_DEFAULT_SCREENS = {
   sm: '640px',
@@ -73,3 +76,38 @@ export function getModifiers(
     })
     .filter((m): m is StyleMediaSizeModifier => m != null)
 }
+
+export function getPropertiesToAppliedModifiersMap(
+  currentClassNameAttribute: string,
+  propertyNames: string[],
+  config: Config | null,
+  context: StylePluginContext,
+): Record<string, StyleModifier[]> {
+  const parseTailwindProperty = parseTailwindPropertyFactory(config, context)
+  const classMapping = getTailwindClassMapping(currentClassNameAttribute.split(' '), config)
+  return propertyNames.reduce((acc, propertyName) => {
+    if (!isStyleInfoKey(propertyName)) {
+      return acc
+    }
+    const parsedProperty = parseTailwindProperty(
+      classMapping[TailwindPropertyMapping[propertyName]],
+      propertyName,
+    )
+    if (parsedProperty?.type == 'property' && parsedProperty.currentVariant.modifiers != null) {
+      return {
+        ...acc,
+        [propertyName]: parsedProperty.currentVariant.modifiers,
+      }
+    } else {
+      return acc
+    }
+  }, {} as Record<string, StyleModifier[]>)
+}
+
+export function getTailwindVariantFromAppliedModifier(
+  appliedModifier: StyleMediaSizeModifier | null,
+): string | null {
+  return appliedModifier?.modifierOrigin?.type === 'tailwind'
+    ? appliedModifier.modifierOrigin.variant
+    : null
+}
diff --git a/editor/src/components/canvas/plugins/tailwind-style-plugin-utils/update-class-list.ts b/editor/src/components/canvas/plugins/tailwind-style-plugin-utils/update-class-list.ts
index b8896c93aa64..d1fb8ab9a044 100644
--- a/editor/src/components/canvas/plugins/tailwind-style-plugin-utils/update-class-list.ts
+++ b/editor/src/components/canvas/plugins/tailwind-style-plugin-utils/update-class-list.ts
@@ -2,7 +2,10 @@ import type { ElementPath } from 'utopia-shared/src/types'
 import { emptyComments } from 'utopia-shared/src/types'
 import { mapDropNulls } from '../../../../core/shared/array-utils'
 import { jsExpressionValue } from '../../../../core/shared/element-template'
-import type { PropertiesToUpdate } from '../../../../core/tailwind/tailwind-class-list-utils'
+import type {
+  PropertiesToRemove,
+  PropertiesToUpdate,
+} from '../../../../core/tailwind/tailwind-class-list-utils'
 import {
   getParsedClassList,
   removeClasses,
@@ -17,6 +20,8 @@ import type { EditorStateWithPatch } from '../../commands/utils/property-utils'
 import { applyValuesAtPath } from '../../commands/utils/property-utils'
 import * as PP from '../../../../core/shared/property-path'
 import type { Config } from 'tailwindcss/types/config'
+import type { StylePluginContext } from '../style-plugins'
+import { getPropertiesToAppliedModifiersMap } from './tailwind-responsive-utils'
 
 export type ClassListUpdate =
   | { type: 'add'; property: string; value: string }
@@ -37,27 +42,54 @@ export const runUpdateClassList = (
   element: ElementPath,
   classNameUpdates: ClassListUpdate[],
   config: Config | null,
+  context: StylePluginContext,
 ): EditorStateWithPatch => {
   const currentClassNameAttribute =
     getClassNameAttribute(getElementFromProjectContents(element, editorState.projectContents))
       ?.value ?? ''
 
+  // this will map every property to the modifiers that are currently affecting it
+  const propertyToAppliedModifiersMap = getPropertiesToAppliedModifiersMap(
+    currentClassNameAttribute,
+    classNameUpdates.map((update) => update.property),
+    config,
+    context,
+  )
+
   const parsedClassList = getParsedClassList(currentClassNameAttribute, config)
 
-  const propertiesToRemove = mapDropNulls(
-    (update) => (update.type !== 'remove' ? null : update.property),
-    classNameUpdates,
+  const propertiesToRemove: PropertiesToRemove = classNameUpdates.reduce(
+    (acc: PropertiesToRemove, val) =>
+      val.type === 'remove'
+        ? {
+            ...acc,
+            [val.property]: {
+              modifiers: propertyToAppliedModifiersMap[val.property] ?? [],
+            },
+          }
+        : acc,
+    {},
   )
 
   const propertiesToUpdate: PropertiesToUpdate = classNameUpdates.reduce(
-    (acc: { [property: string]: string }, val) =>
-      val.type === 'remove' ? acc : { ...acc, [val.property]: val.value },
+    (acc: PropertiesToUpdate, val) =>
+      val.type === 'remove'
+        ? acc
+        : {
+            ...acc,
+            [val.property]: {
+              newValue: val.value,
+              modifiers: propertyToAppliedModifiersMap[val.property] ?? [],
+            },
+          },
     {},
   )
 
   const updatedClassList = [
     removeClasses(propertiesToRemove),
     updateExistingClasses(propertiesToUpdate),
+    // currently we're not adding new breakpoint styles (but only editing current ones),
+    // so we don't need to pass the propertyToAppliedModifiersMap here
     addNewClasses(propertiesToUpdate),
   ].reduce((classList, fn) => fn(classList), parsedClassList)
 
diff --git a/editor/src/components/canvas/plugins/tailwind-style-plugin.ts b/editor/src/components/canvas/plugins/tailwind-style-plugin.ts
index 5f378167a27c..2218753fdb26 100644
--- a/editor/src/components/canvas/plugins/tailwind-style-plugin.ts
+++ b/editor/src/components/canvas/plugins/tailwind-style-plugin.ts
@@ -279,6 +279,7 @@ export const TailwindPlugin = (config: Config | null): StylePlugin => ({
       elementPath,
       [...propsToDelete, ...propsToSet],
       config,
+      { sceneSize: getContainingSceneSize(elementPath, editorState.jsxMetadata) },
     )
   },
 })
diff --git a/editor/src/core/tailwind/tailwind-class-list-utils.spec.ts b/editor/src/core/tailwind/tailwind-class-list-utils.spec.ts
index ca8816febed2..6b1594367774 100644
--- a/editor/src/core/tailwind/tailwind-class-list-utils.spec.ts
+++ b/editor/src/core/tailwind/tailwind-class-list-utils.spec.ts
@@ -141,7 +141,10 @@ describe('tailwind class list utils', () => {
   describe('removing classes', () => {
     it('can remove property', () => {
       const classList = getParsedClassList('p-4 m-2 text-white w-4 flex flex-row', null)
-      const updatedClassList = removeClasses(['padding', 'textColor'])(classList)
+      const updatedClassList = removeClasses({
+        padding: { modifiers: [] },
+        textColor: { modifiers: [] },
+      })(classList)
       expect(getClassListFromParsedClassList(updatedClassList, null)).toMatchInlineSnapshot(
         `"m-2 w-4 flex flex-row"`,
       )
@@ -151,7 +154,10 @@ describe('tailwind class list utils', () => {
         'p-4 m-2 text-white hover:text-red-100 w-4 flex flex-row',
         null,
       )
-      const updatedClassList = removeClasses(['padding', 'textColor'])(classList)
+      const updatedClassList = removeClasses({
+        padding: { modifiers: [] },
+        textColor: { modifiers: [] },
+      })(classList)
       expect(getClassListFromParsedClassList(updatedClassList, null)).toMatchInlineSnapshot(
         `"m-2 hover:text-red-100 w-4 flex flex-row"`,
       )
@@ -162,8 +168,8 @@ describe('tailwind class list utils', () => {
     it('can update class in class list', () => {
       const classList = getParsedClassList('p-4 m-2 text-white w-4 flex flex-row', null)
       const updatedClassList = updateExistingClasses({
-        flexDirection: 'column',
-        width: '23px',
+        flexDirection: { newValue: 'column', modifiers: [] },
+        width: { newValue: '23px', modifiers: [] },
       })(classList)
       expect(getClassListFromParsedClassList(updatedClassList, null)).toMatchInlineSnapshot(
         `"p-4 m-2 text-white w-[23px] flex flex-col"`,
@@ -171,7 +177,9 @@ describe('tailwind class list utils', () => {
     })
     it('does not remove property with selector', () => {
       const classList = getParsedClassList('p-4 hover:p-6 m-2 text-white w-4 flex flex-row', null)
-      const updatedClassList = updateExistingClasses({ padding: '8rem' })(classList)
+      const updatedClassList = updateExistingClasses({
+        padding: { newValue: '8rem', modifiers: [] },
+      })(classList)
       expect(getClassListFromParsedClassList(updatedClassList, null)).toMatchInlineSnapshot(
         `"p-32 hover:p-6 m-2 text-white w-4 flex flex-row"`,
       )
@@ -182,9 +190,9 @@ describe('tailwind class list utils', () => {
     it('can add new class to class list', () => {
       const classList = getParsedClassList('p-4 m-2 text-white w-4 flex flex-row', null)
       const updatedClassList = addNewClasses({
-        backgroundColor: 'white',
-        justifyContent: 'space-between',
-        positionLeft: '-20px',
+        backgroundColor: { newValue: 'white', modifiers: [] },
+        justifyContent: { newValue: 'space-between', modifiers: [] },
+        positionLeft: { newValue: '-20px', modifiers: [] },
       })(classList)
       expect(getClassListFromParsedClassList(updatedClassList, null)).toMatchInlineSnapshot(
         `"p-4 m-2 text-white w-4 flex flex-row bg-white justify-between -left-[20px]"`,
diff --git a/editor/src/core/tailwind/tailwind-class-list-utils.ts b/editor/src/core/tailwind/tailwind-class-list-utils.ts
index fd6152c79f32..926ec33600f1 100644
--- a/editor/src/core/tailwind/tailwind-class-list-utils.ts
+++ b/editor/src/core/tailwind/tailwind-class-list-utils.ts
@@ -1,11 +1,12 @@
 import * as TailwindClassParser from '@xengine/tailwindcss-class-parser'
 import type { Config } from 'tailwindcss/types/config'
 import { mapDropNulls } from '../shared/array-utils'
+import type { StyleMediaSizeModifier, StyleModifier } from '../../components/canvas/canvas-types'
 
 export type ParsedTailwindClass = {
   property: string
   value: string
-  variants: unknown[]
+  variants: { type: string; value: string }[]
   negative: boolean
 } & Record<string, unknown>
 
@@ -49,7 +50,13 @@ export type ClassListTransform = (
 ) => TailwindClassParserResult[]
 
 export interface PropertiesToUpdate {
-  [property: string]: string
+  [property: string]: { newValue: string; modifiers: StyleModifier[] }
+}
+
+export interface PropertiesToRemove {
+  [property: string]: {
+    modifiers: StyleModifier[]
+  }
 }
 
 export const addNewClasses =
@@ -60,12 +67,12 @@ export const addNewClasses =
     )
 
     const newClasses: TailwindClassParserResult[] = mapDropNulls(
-      ([prop, value]) =>
+      ([prop, update]) =>
         existingProperties.has(prop)
           ? null
           : {
               type: 'parsed',
-              ast: { property: prop, value: value, variants: [], negative: false },
+              ast: { property: prop, value: update.newValue, variants: [], negative: false },
             },
       Object.entries(propertiesToAdd),
     )
@@ -78,30 +85,79 @@ export const updateExistingClasses =
   (propertiesToUpdate: PropertiesToUpdate): ClassListTransform =>
   (parsedClassList: TailwindClassParserResult[]) => {
     const classListWithUpdatedClasses: TailwindClassParserResult[] = parsedClassList.map((cls) => {
-      if (cls.type !== 'parsed' || cls.ast.variants.length > 0) {
-        return cls
-      }
-      const updatedProperty = propertiesToUpdate[cls.ast.property]
-      if (updatedProperty == null) {
+      if (!shouldUpdateClass(cls, propertiesToUpdate)) {
         return cls
       }
+      const propertyToUpdate = propertiesToUpdate[cls.ast.property]
       return {
         type: 'parsed',
-        ast: { property: cls.ast.property, value: updatedProperty, variants: [], negative: false },
+        ast: {
+          property: cls.ast.property,
+          value: propertyToUpdate.newValue,
+          variants: cls.ast.variants,
+          negative: false,
+        },
       }
     })
     return classListWithUpdatedClasses
   }
 
 export const removeClasses =
-  (propertiesToRemove: string[]): ClassListTransform =>
+  (propertiesToRemove: PropertiesToRemove): ClassListTransform =>
   (parsedClassList: TailwindClassParserResult[]) => {
-    const propertiesToRemoveSet = new Set(propertiesToRemove)
     const classListWithRemovedClasses = parsedClassList.filter((cls) => {
-      if (cls.type !== 'parsed' || cls.ast.variants.length > 0) {
+      if (!shouldUpdateClass(cls, propertiesToRemove)) {
         return cls
       }
-      return !propertiesToRemoveSet.has(cls.ast.property)
+      return propertiesToRemove[cls.ast.property] != null
     })
     return classListWithRemovedClasses
   }
+
+function getTailwindSizeVariant(modifiers: StyleModifier[]): string | null {
+  const mediaModifier = modifiers.find((m): m is StyleMediaSizeModifier => m.type === 'media-size')
+  if (mediaModifier == null) {
+    return null
+  }
+  if (mediaModifier.modifierOrigin?.type !== 'tailwind') {
+    return null
+  }
+  return mediaModifier.modifierOrigin.variant
+}
+
+function shouldUpdateClass(
+  cls: TailwindClassParserResult,
+  propertiesToUpdate: PropertiesToUpdate | PropertiesToRemove,
+): cls is TailwindClassParserResult & { type: 'parsed' } {
+  if (cls.type !== 'parsed') {
+    return false
+  }
+  const propertyToUpdate = propertiesToUpdate[cls.ast.property]
+  if (propertyToUpdate == null) {
+    // this property is not in the list
+    return false
+  }
+  const sizeVariantToUpdate = getTailwindSizeVariant(propertyToUpdate.modifiers)
+  if (
+    sizeVariantToUpdate == null &&
+    cls.ast.variants.filter((v) => v.type === 'media').length > 0
+  ) {
+    // we need to update the default property value but this class has size variants
+    return false
+  }
+  if (
+    sizeVariantToUpdate != null &&
+    !variantsHasMediaSizeVariant(cls.ast.variants, sizeVariantToUpdate)
+  ) {
+    // we need to update a specific size variant but this class doesn't have it
+    return false
+  }
+  return true
+}
+
+function variantsHasMediaSizeVariant(
+  variants: { type: string; value: string }[],
+  sizeVariant: string,
+): boolean {
+  return variants.some((v) => v.type === 'media' && v.value === sizeVariant)
+}