diff --git a/src/trix/controllers/level_2_input_controller.js b/src/trix/controllers/level_2_input_controller.js
index a83cf6760..c6a674bce 100644
--- a/src/trix/controllers/level_2_input_controller.js
+++ b/src/trix/controllers/level_2_input_controller.js
@@ -363,7 +363,6 @@ export default class Level2InputController extends InputController {
 
       const href = dataTransfer.getData("URL")
       const html = dataTransfer.getData("text/html")
-      const file = dataTransfer.files?.[0]
 
       if (href) {
         let string
@@ -394,9 +393,9 @@ export default class Level2InputController extends InputController {
         this.afterRender = () => {
           return this.delegate?.inputControllerDidPaste(paste)
         }
-      } else if (file && !dataTransferIsMsOfficePaste(dataTransfer)) {
+      } else if (processableFilePaste(this.event)) {
         paste.type = "File"
-        paste.file = file
+        paste.file = dataTransfer.files[0]
         this.delegate?.inputControllerWillPaste(paste)
         this.withTargetDOMRange(function() {
           return this.responder?.insertFile(paste.file)
@@ -582,10 +581,20 @@ const staticRangeToRange = function(staticRange) {
 
 const dragEventHasFiles = (event) => Array.from(event.dataTransfer?.types || []).includes("Files")
 
+const processableFilePaste = (event) => {
+  // Paste events that only have files are handled by the paste event handler,
+  // to work around Safari not supporting beforeinput.insertFromPaste for files.
+
+  // MS Office text pastes include a file with a screenshot of the text, but we should
+  // handle them as text pastes.
+  return event.dataTransfer.files?.[0] && !pasteEventHasFilesOnly(event) && !dataTransferIsMsOfficePaste(event)
+}
+
 const pasteEventHasFilesOnly = function(event) {
   const clipboard = event.clipboardData
   if (clipboard) {
-    return clipboard.types.includes("Files") && clipboard.types.length === 1 && clipboard.files.length >= 1
+    const fileTypes = Array.from(clipboard.types).filter((type) => type.match(/file/i)) // "Files", "application/x-moz-file"
+    return fileTypes.length === clipboard.types.length && clipboard.files.length >= 1
   }
 }
 
diff --git a/src/trix/core/helpers/events.js b/src/trix/core/helpers/events.js
index 0565a608d..4248830d3 100644
--- a/src/trix/core/helpers/events.js
+++ b/src/trix/core/helpers/events.js
@@ -14,7 +14,7 @@ export const dataTransferIsPlainText = function(dataTransfer) {
   }
 }
 
-export const dataTransferIsMsOfficePaste = function(dataTransfer) {
+export const dataTransferIsMsOfficePaste = ({ dataTransfer }) => {
   return dataTransfer.types.includes("Files") &&
     dataTransfer.types.includes("text/html") &&
     dataTransfer.getData("text/html").includes("urn:schemas-microsoft-com:office:office")