diff --git a/src/internal/connector/exchange/exchange_service_test.go b/src/internal/connector/exchange/exchange_service_test.go
index 83ae9a8ec..994078462 100644
--- a/src/internal/connector/exchange/exchange_service_test.go
+++ b/src/internal/connector/exchange/exchange_service_test.go
@@ -394,6 +394,10 @@ func (suite *ExchangeServiceSuite) TestRestoreMessages() {
 			name:  "One Direct Attachment",
 			bytes: mockconnector.GetMockMessageWithDirectAttachment(folderName),
 		},
+		{
+			name:  "Two Attachments",
+			bytes: mockconnector.GetMockMessageWithTwoAttachments(folderName),
+		},
 	}
 
 	for _, test := range tests {
@@ -405,7 +409,7 @@ func (suite *ExchangeServiceSuite) TestRestoreMessages() {
 				folderID,
 				userID,
 			)
-			require.NoError(t, err)
+			require.NoError(t, err, support.ConnectorStackErrorTrace(err))
 		})
 	}
 
diff --git a/src/internal/connector/exchange/service_restore.go b/src/internal/connector/exchange/service_restore.go
index ecfaa7eed..9f2084257 100644
--- a/src/internal/connector/exchange/service_restore.go
+++ b/src/internal/connector/exchange/service_restore.go
@@ -236,6 +236,16 @@ func SendMailToBackStore(
 	user, destination string,
 	message models.Messageable,
 ) error {
+	var (
+		attached []models.Attachmentable
+		errs     error
+	)
+
+	if *message.GetHasAttachments() {
+		attached = message.GetAttachments()
+		message.SetAttachments([]models.Attachmentable{})
+	}
+
 	sentMessage, err := service.Client().UsersById(user).MailFoldersById(destination).Messages().Post(ctx, message, nil)
 	if err != nil {
 		return errors.Wrap(err,
@@ -247,6 +257,26 @@ func SendMailToBackStore(
 		return errors.New("message not Sent: blocked by server")
 	}
 
+	if len(attached) > 0 {
+		id := *sentMessage.GetId()
+		for _, attachment := range attached {
+			_, err = service.Client().
+				UsersById(user).
+				MailFoldersById(destination).
+				MessagesById(id).
+				Attachments().
+				Post(ctx, attachment, nil)
+			if err != nil {
+				errs = support.WrapAndAppend(id,
+					err,
+					errs,
+				)
+			}
+		}
+
+		return errs
+	}
+
 	return nil
 }
 
diff --git a/src/internal/connector/mockconnector/mock_data_message.go b/src/internal/connector/mockconnector/mock_data_message.go
index a4e555de1..03fd439a3 100644
--- a/src/internal/connector/mockconnector/mock_data_message.go
+++ b/src/internal/connector/mockconnector/mock_data_message.go
@@ -186,6 +186,25 @@ func GetMessageWithOneDriveAttachment(subject string) []byte {
 	return []byte(message)
 }
 
+// GetMockMessageWithTwoAttachments returns byte representation of message with two attachments
+// Serialized with: kiota-serialization-json-go v0.7.1
+func GetMockMessageWithTwoAttachments(subject string) []byte {
+	//nolint:lll
+	message := "{\"id\":\"AAMkAGZmNjNlYjI3LWJlZWYtNGI4Mi04YjMyLTIxYThkNGQ4NmY1MwBGAAAAAADCNgjhM9QmQYWNcI7hCpPrBwDSEBNbUIB9RL6ePDeF3FIYAAAAAAEMAADSEBNbUIB9RL6ePDeF3FIYAAB6LpD0AAA=\",\"@odata.type\":\"#microsoft.graph.message\",\"@odata.etag\":\"W/\\\"CQAAABYAAADSEBNbUIB9RL6ePDeF3FIYAAB5JBpO\\\"\",\"@odata.context\":\"https://graph.microsoft.com/v1.0/$metadata#users('a4a472f8-ccb0-43ec-bf52-3697a91b926c')/messages/$entity\",\"categories\":[],\"changeKey\":\"CQAAABYAAADSEBNbUIB9RL6ePDeF3FIYAAB5JBpO\"," +
+		"\"createdDateTime\":\"2022-09-30T20:31:22Z\",\"lastModifiedDateTime\":\"2022-09-30T20:31:25Z\",\"attachments\":[{\"id\":\"AAMkAGZmNjNlYjI3LWJlZWYtNGI4Mi04YjMyLTIxYThkNGQ4NmY1MwBGAAAAAADCNgjhM9QmQYWNcI7hCpPrBwDSEBNbUIB9RL6ePDeF3FIYAAAAAAEMAADSEBNbUIB9RL6ePDeF3FIYAAB6LpD0AAABEgAQAMIBac0_D4pPgtgr9mhVWaM=\",\"@odata.type\":\"#microsoft.graph.fileAttachment\",\"@odata.mediaContentType\":\"text/plain\",\"contentType\":\"text/plain\",\"isInline\":false,\"lastModifiedDateTime\":\"2022-09-30T20:31:22Z\"," +
+		"\"name\":\"sample.txt\",\"size\":198,\"contentBytes\":\"VFBTIFJlcG9ydHMgYXJlIGZvciB3aW5uZXJzCg==\"},{\"id\":\"AAMkAGZmNjNlYjI3LWJlZWYtNGI4Mi04YjMyLTIxYThkNGQ4NmY1MwBGAAAAAADCNgjhM9QmQYWNcI7hCpPrBwDSEBNbUIB9RL6ePDeF3FIYAAAAAAEMAADSEBNbUIB9RL6ePDeF3FIYAAB6LpD0AAABEgAQAHO2tnfyTF1HnQKqNSMCO7A=\",\"@odata.type\":\"#microsoft.graph.fileAttachment\",\"@odata.mediaContentType\":\"text/plain\",\"contentType\":\"text/plain\",\"isInline\":false,\"lastModifiedDateTime\":\"2022-09-30T20:31:22Z\"," +
+		"\"name\":\"sample3.txt\",\"size\":234,\"contentBytes\":\"SWYgdGhlIGZvcmNlIGlzIHdpdGggeW91LCBpdCdzIHdpdGggeW91LiBOb3Qgb25seSBpbiBNYXkuCg==\"}],\"bccRecipients\":[],\"body\":{\"content\":\"<html><head>\\r\\n<meta http-equiv=\\\"Content-Type\\\" content=\\\"text/html; charset=utf-8\\\"><style type=\\\"text/css\\\" style=\\\"display:none\\\">\\r\\n<!--\\r\\np\\r\\n\\t{margin-top:0;\\r\\n\\tmargin-bottom:0}\\r\\n-->\\r\\n</style></head><body dir=\\\"ltr\\\"><div class=\\\"elementToProof\\\" " +
+		"style=\\\"font-family:Calibri,Arial,Helvetica,sans-serif; font-size:12pt; color:rgb(0,0,0)\\\">Lidia,</div><div class=\\\"elementToProof\\\" style=\\\"font-family:Calibri,Arial,Helvetica,sans-serif; font-size:12pt; color:rgb(0,0,0)\\\"><br></div><div class=\\\"elementToProof\\\" style=\\\"font-family:Calibri,Arial,Helvetica,sans-serif; font-size:12pt; color:rgb(0,0,0)\\\">We have to decide between two items for our speech writers to go over. Please let me know which is the best for the " +
+		"upcoming retreat.&nbsp;</div><div class=\\\"elementToProof\\\" style=\\\"font-family:Calibri,Arial,Helvetica,sans-serif; font-size:12pt; color:rgb(0,0,0)\\\"><br></div><div class=\\\"elementToProof\\\" style=\\\"font-family:Calibri,Arial,Helvetica,sans-serif; font-size:12pt; color:rgb(0,0,0)\\\">Best,&nbsp;</div><div class=\\\"elementToProof\\\" style=\\\"font-family:Calibri,Arial,Helvetica,sans-serif; font-size:12pt; color:rgb(0,0,0)\\\"><br></div><div class=\\\"elementToProof\\\" " +
+		"style=\\\"font-family:Calibri,Arial,Helvetica,sans-serif; font-size:12pt; color:rgb(0,0,0)\\\">Dustin</div></body></html>\",\"contentType\":\"html\",\"@odata.type\":\"#microsoft.graph.itemBody\"},\"bodyPreview\":\"Lidia,\\r\\n\\r\\nWe have to decide between two items for our speech writers to go over. Please let me know which is the best for the upcoming retreat.\\r\\n\\r\\nBest,\\r\\n\\r\\nDustin\",\"ccRecipients\":[]," +
+		"\"conversationId\":\"AAQkAGZmNjNlYjI3LWJlZWYtNGI4Mi04YjMyLTIxYThkNGQ4NmY1MwAQANHUb9Zc-aBAvBW5io77k-g=\",\"conversationIndex\":\"AQHY1Qss0dRv1lz9oEC8FbmKjvuT+A==\",\"flag\":{\"flagStatus\":\"notFlagged\",\"@odata.type\":\"#microsoft.graph.followupFlag\"},\"from\":{\"emailAddress\":{\"address\":\"dustina@8qzvrj.onmicrosoft.com\",\"name\":\"Dustin Abbot\",\"@odata.type\":\"#microsoft.graph.emailAddress\"},\"@odata.type\":\"#microsoft.graph.recipient\"},\"hasAttachments\":true," +
+		"\"importance\":\"normal\",\"inferenceClassification\":\"focused\",\"internetMessageId\":\"<SJ0PR17MB5622DB7B5847BF4BE7965B32C3569@SJ0PR17MB5622.namprd17.prod.outlook.com>\",\"isDeliveryReceiptRequested\":false,\"isDraft\":false,\"isRead\":false,\"isReadReceiptRequested\":false,\"parentFolderId\":\"AAMkAGZmNjNlYjI3LWJlZWYtNGI4Mi04YjMyLTIxYThkNGQ4NmY1MwAuAAAAAADCNgjhM9QmQYWNcI7hCpPrAQDSEBNbUIB9RL6ePDeF3FIYAAAAAAEMAAA=\",\"receivedDateTime\":\"2022-09-30T20:31:23Z\",\"replyTo\":[]," +
+		"\"sender\":{\"emailAddress\":{\"address\":\"dustina@8qzvrj.onmicrosoft.com\",\"name\":\"Dustin Abbot\",\"@odata.type\":\"#microsoft.graph.emailAddress\"},\"@odata.type\":\"#microsoft.graph.recipient\"},\"sentDateTime\":\"2022-09-30T20:31:19Z\"," +
+		"\"subject\":\"" + subject + "\",\"toRecipients\":[{\"emailAddress\":{\"address\":\"LidiaH@8qzvrj.onmicrosoft.com\",\"name\":\"Lidia Holloway\",\"@odata.type\":\"#microsoft.graph.emailAddress\"},\"@odata.type\":\"#microsoft.graph.recipient\"}],\"webLink\":\"https://outlook.office365.com/owa/?ItemID=AAMkAGZmNjNlYjI3LWJlZWYtNGI4Mi04YjMyLTIxYThkNGQ4NmY1MwBGAAAAAADCNgjhM9QmQYWNcI7hCpPrBwDSEBNbUIB9RL6ePDeF3FIYAAAAAAEMAADSEBNbUIB9RL6ePDeF3FIYAAB6LpD0AAA%3D&exvsurl=1&viewmodel=ReadMessageItem\"}"
+
+	return []byte(message)
+}
+
 // GetMockContactBytes returns bytes for Contactable item.
 // When hydrated: contact.GetGivenName() shows differences
 func GetMockContactBytes(middleName string) []byte {