diff --git a/src/lib/media/util.ts b/src/lib/media/util.ts
index a27c71d826..4eee6a72fb 100644
--- a/src/lib/media/util.ts
+++ b/src/lib/media/util.ts
@@ -5,3 +5,69 @@ export function extractDataUriMime(uri: string): string {
 export function getDataUriSize(uri: string): number {
   return Math.round((uri.length * 3) / 4) // very rough estimate
 }
+
+// TODO: Can we consolidate this with an existing type?
+interface ImageInfo {
+  uri: string
+  width: number
+  height: number
+}
+
+/**
+ * Given a File instance (like one pulled from a paste event), return
+ * a data URI and the image dimensions for the pasted file. Returns
+ * width 0, height 0 for non-images
+ */
+export function getImageInfoFromFile(file: File): Promise<ImageInfo> {
+  return new Promise((resolve, reject) => {
+    const reader = new FileReader()
+    reader.readAsDataURL(file)
+    reader.onloadend = () => {
+      const maybeUri = reader.result
+
+      // reader.result can be different data types depending on what
+      // readAs... method is called. We're using readAsDataUrl which
+      // will read as a string. If someone were to change that
+      // accidentally or otherwise, then reader.result might not be
+      // a string. In which case, we'll bail out and yell at the dev.
+      if (typeof maybeUri === 'string') {
+        const uri = maybeUri
+
+        // Non-images proooobably shouldn't even be accepted in this function
+        // TODO: Maybe just reject for non-images?
+        if (!file.type.startsWith('image/')) {
+          return resolve({
+            uri,
+            width: 0,
+            height: 0,
+          })
+        }
+
+        // Get the dimensions of said file
+        const img = new Image()
+        img.src = uri
+        img.onload = () => {
+          return resolve({
+            uri,
+            width: img.width,
+            height: img.height,
+          })
+        }
+
+        return
+      }
+
+      reject(
+        new Error(
+          'File was not called with .readAsDataURL(...). ' +
+            'This absolutely should not happen. Make sure ' +
+            'the reader instance is calling .readAsDataURL() ' +
+            'on the file',
+        ),
+      )
+    }
+
+    reader.onerror = reject
+    reader.onabort = () => reject(new Error('File read aborted'))
+  })
+}
diff --git a/src/view/com/composer/Composer.tsx b/src/view/com/composer/Composer.tsx
index 6009debdd1..bf04643879 100644
--- a/src/view/com/composer/Composer.tsx
+++ b/src/view/com/composer/Composer.tsx
@@ -130,9 +130,17 @@ export const ComposePost = observer(function ComposePost({
       if (selectedPhotos.length >= 4) {
         return
       }
-      onSelectPhotos([...selectedPhotos, uri])
+
+      setSelectedPhotos(sp => {
+        if (sp.length >= 4) {
+          return sp
+        }
+
+        track('Composer:SelectedPhotos')
+        return [...sp, uri]
+      })
     },
-    [selectedPhotos, onSelectPhotos],
+    [selectedPhotos, setSelectedPhotos, track],
   )
 
   const onPressPublish = React.useCallback(async () => {
diff --git a/src/view/com/composer/text-input/TextInput.web.tsx b/src/view/com/composer/text-input/TextInput.web.tsx
index ad891fa5bf..80ff5849fe 100644
--- a/src/view/com/composer/text-input/TextInput.web.tsx
+++ b/src/view/com/composer/text-input/TextInput.web.tsx
@@ -11,6 +11,15 @@ import {Text} from '@tiptap/extension-text'
 import isEqual from 'lodash.isequal'
 import {UserAutocompleteViewModel} from 'state/models/user-autocomplete-view'
 import {createSuggestion} from './web/Autocomplete'
+import {Transaction} from '@tiptap/pm/state'
+import {cropAndCompressFlow} from 'lib/media/picker'
+import {useStores} from 'state/index'
+import {
+  POST_IMG_MAX_HEIGHT,
+  POST_IMG_MAX_SIZE,
+  POST_IMG_MAX_WIDTH,
+} from 'lib/constants'
+import {getImageInfoFromFile} from 'lib/media/util'
 
 export interface TextInputRef {
   focus: () => void
@@ -36,12 +45,28 @@ export const TextInput = React.forwardRef(
       suggestedLinks,
       autocompleteView,
       setRichText,
-      // onPhotoPasted, TODO
+      onPhotoPasted,
       onSuggestedLinksChanged,
     }: // onError, TODO
     TextInputProps,
     ref,
   ) => {
+    const store = useStores()
+    const processClipboardItemAsPhoto = async (item: DataTransferItem) => {
+      const file = item.getAsFile()
+
+      if (file && file.type && file.type.startsWith('image/')) {
+        const {uri, width, height} = await getImageInfoFromFile(file)
+        const croppedUri = await cropAndCompressFlow(
+          store,
+          uri,
+          {width, height},
+          {width: POST_IMG_MAX_WIDTH, height: POST_IMG_MAX_HEIGHT},
+          POST_IMG_MAX_SIZE,
+        )
+        onPhotoPasted(croppedUri)
+      }
+    }
     const editor = useEditor({
       extensions: [
         Document,
@@ -65,6 +90,29 @@ export const TextInput = React.forwardRef(
       autofocus: true,
       editable: true,
       injectCSS: true,
+      editorProps: {
+        handlePaste(_, event) {
+          // It's possible to copy a single screenshot or multiple files
+          // In the case of a single screenshot (e.g. cmd+shift+4), this
+          // list will be length 1. In the case of selecting multiple
+          // files in a file explorer and copying/pasting, this will be
+          // those list of copied files
+          const items = event.clipboardData?.items
+
+          // Let tiptap know to fallback to default paste behavior
+          if (!items || items.length === 0) {
+            return false
+          }
+
+          // For any pasted images, bring them through the crop and compress flow
+          for (const item of Array.from(items)) {
+            processClipboardItemAsPhoto(item)
+          }
+
+          // Let tiptap know that we handled the paste event
+          return true
+        },
+      },
       onUpdate({editor: editorProp}) {
         const json = editorProp.getJSON()