diff --git a/imessage/interface.go b/imessage/interface.go
index 423ab6bd..1af22deb 100644
--- a/imessage/interface.go
+++ b/imessage/interface.go
@@ -65,7 +65,7 @@ type API interface {
 	PrepareDM(guid string) error
 
 	SendMessage(chatID, text string, replyTo string, replyToPart int, richLink *RichLink, metadata MessageMetadata) (*SendResponse, error)
-	SendFile(chatID, text, filename string, pathOnDisk string, replyTo string, replyToPart int, mimeType string, voiceMemo bool, metadata MessageMetadata) (*SendResponse, error)
+	SendFile(chatID, text, filename string, pathOnDisk, guid string, replyTo string, replyToPart int, mimeType string, voiceMemo bool, metadata MessageMetadata) (*SendResponse, error)
 	SendFileCleanup(sendFileDir string)
 	SendTapback(chatID, targetGUID string, targetPart int, tapback TapbackType, remove bool) (*SendResponse, error)
 	SendReadReceipt(chatID, readUpTo string) error
@@ -81,6 +81,11 @@ type API interface {
 	Capabilities() ConnectorCapabilities
 }
 
+type FilePreparingAPI interface {
+	API
+	SendFilePrepare(filename string, data []byte) (dir, guid string, err error)
+}
+
 var TempFilePermissions os.FileMode = 0640
 var TempDirPermissions os.FileMode = 0700
 
diff --git a/imessage/ios/ipc.go b/imessage/ios/ipc.go
index 8381fd64..7c5faa4b 100644
--- a/imessage/ios/ipc.go
+++ b/imessage/ios/ipc.go
@@ -71,6 +71,7 @@ func timeToFloat(time time.Time) float64 {
 type APIWithIPC interface {
 	imessage.API
 	SetIPC(*ipc.Processor)
+	GetIPC() *ipc.Processor
 	SetContactProxy(api imessage.ContactAPI)
 	SetChatInfoProxy(api imessage.ChatInfoAPI)
 }
@@ -121,6 +122,10 @@ func (ios *iOSConnector) SetIPC(proc *ipc.Processor) {
 	ios.IPC = proc
 }
 
+func (ios *iOSConnector) GetIPC() *ipc.Processor {
+	return ios.IPC
+}
+
 func (ios *iOSConnector) SetContactProxy(api imessage.ContactAPI) {
 	ios.contactProxy = api
 }
@@ -517,12 +522,13 @@ func (ios *iOSConnector) SendMessage(chatID, text string, replyTo string, replyT
 	return &resp, err
 }
 
-func (ios *iOSConnector) SendFile(chatID, text, filename string, pathOnDisk string, replyTo string, replyToPart int, mimeType string, voiceMemo bool, metadata imessage.MessageMetadata) (*imessage.SendResponse, error) {
+func (ios *iOSConnector) SendFile(chatID, text, filename, pathOnDisk, guid, replyTo string, replyToPart int, mimeType string, voiceMemo bool, metadata imessage.MessageMetadata) (*imessage.SendResponse, error) {
 	var resp imessage.SendResponse
 	err := ios.IPC.Request(context.Background(), ReqSendMedia, &SendMediaRequest{
 		ChatGUID: chatID,
 		Text:     text,
 		Attachment: imessage.Attachment{
+			GUID:       guid,
 			FileName:   filename,
 			PathOnDisk: pathOnDisk,
 			MimeType:   mimeType,
diff --git a/imessage/ios/requests.go b/imessage/ios/requests.go
index e095e426..da0ea78c 100644
--- a/imessage/ios/requests.go
+++ b/imessage/ios/requests.go
@@ -25,6 +25,7 @@ import (
 
 const (
 	ReqSendMessage         ipc.Command = "send_message"
+	ReqUploadMedia         ipc.Command = "upload_media"
 	ReqSendMedia           ipc.Command = "send_media"
 	ReqSendTapback         ipc.Command = "send_tapback"
 	ReqSendReadReceipt     ipc.Command = "send_read_receipt"
@@ -66,6 +67,14 @@ type SendMediaRequest struct {
 	Metadata       imessage.MessageMetadata `json:"metadata,omitempty"`
 }
 
+type UploadMediaRequest struct {
+	PathOnDisk string `json:"path_on_disk"`
+}
+
+type UploadMediaResponse struct {
+	GUID string `json:"guid"`
+}
+
 type SendTapbackRequest struct {
 	ChatGUID   string               `json:"chat_guid"`
 	TargetGUID string               `json:"target_guid"`
diff --git a/imessage/mac-nosip/nosip.go b/imessage/mac-nosip/nosip.go
index 0b92325e..79d28767 100644
--- a/imessage/mac-nosip/nosip.go
+++ b/imessage/mac-nosip/nosip.go
@@ -17,6 +17,7 @@
 package mac_nosip
 
 import (
+	"context"
 	"encoding/json"
 	"errors"
 	"fmt"
@@ -320,6 +321,22 @@ func (mac *MacNoSIPConnector) Capabilities() imessage.ConnectorCapabilities {
 	}
 }
 
+func (mac *MacNoSIPConnector) SendFilePrepare(filename string, data []byte) (string, string, error) {
+	dir, path, err := imessage.SendFilePrepare(filename, data)
+	if err != nil {
+		return dir, "", fmt.Errorf("failed to write file to disk: %w", err)
+	}
+	var resp ios.UploadMediaResponse
+	ctx := context.Background()
+	err = mac.GetIPC().Request(ctx, ios.ReqUploadMedia, &ios.UploadMediaRequest{
+		PathOnDisk: path,
+	}, &resp)
+	if err != nil {
+		return dir, "", fmt.Errorf("failed to upload file: %w", err)
+	}
+	return dir, resp.GUID, nil
+}
+
 func init() {
 	imessage.Implementations["mac-nosip"] = NewMacNoSIPConnector
 }
diff --git a/imessage/mac/send.go b/imessage/mac/send.go
index 5c634f0d..5326c13f 100644
--- a/imessage/mac/send.go
+++ b/imessage/mac/send.go
@@ -182,7 +182,7 @@ func (mac *macOSDatabase) SendMessage(chatID, text string, replyTo string, reply
 	return nil, mac.sendMessageWithRetry(sendMessage, sendMessageWithService, sendMessageBuddy, imessage.ParseIdentifier(chatID), text)
 }
 
-func (mac *macOSDatabase) SendFile(chatID, text, filename string, pathOnDisk string, replyTo string, replyToPart int, mimeType string, voiceMemo bool, metadata imessage.MessageMetadata) (*imessage.SendResponse, error) {
+func (mac *macOSDatabase) SendFile(chatID, text, filename, pathOnDisk, guid, replyTo string, replyToPart int, mimeType string, voiceMemo bool, metadata imessage.MessageMetadata) (*imessage.SendResponse, error) {
 	if voiceMemo {
 		mac.log.Warn("received a request to send a file as a voice memo, but mac does not support this. sending as regular attachment.")
 	}
diff --git a/portal.go b/portal.go
index 60105666..3adcfda8 100644
--- a/portal.go
+++ b/portal.go
@@ -1313,8 +1313,13 @@ func (portal *Portal) handleMatrixMediaDirect(url id.ContentURI, file *event.Enc
 		}
 	}
 
-	var dir, filePath string
-	dir, filePath, err = imessage.SendFilePrepare(filename, data)
+	var dir, filePath, guid string
+	prep, ok := portal.bridge.IM.(imessage.FilePreparingAPI)
+	if ok {
+		dir, guid, err = prep.SendFilePrepare(filename, data)
+	} else {
+		dir, filePath, err = imessage.SendFilePrepare(filename, data)
+	}
 	if err != nil {
 		portal.log.Errorfln("failed to prepare to send file: %w", err)
 		return
@@ -1333,7 +1338,7 @@ func (portal *Portal) handleMatrixMediaDirect(url id.ContentURI, file *event.Enc
 		}
 	}
 
-	resp, err = portal.bridge.IM.SendFile(portal.getTargetGUID("media message", evt.ID, ""), caption, filename, filePath, messageReplyID, messageReplyPart, mimeType, isVoiceMemo, metadata)
+	resp, err = portal.bridge.IM.SendFile(portal.getTargetGUID("media message", evt.ID, ""), caption, filename, filePath, guid, messageReplyID, messageReplyPart, mimeType, isVoiceMemo, metadata)
 	portal.bridge.IM.SendFileCleanup(dir)
 	return
 }