diff --git a/CHANGELOG.md b/CHANGELOG.md
index 7209851ac..1580ef6df 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -10,6 +10,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 ### Fixed
 - Handle the case where an email cannot be retrieved from Exchange due to an `ErrorInvalidRecipients` error. In
 this case, Corso will skip over the item but report this in the backup summary.
+- Guarantee Exchange email restoration when restoring multiple attachments. Some previous restores were failing with `ErrorItemNotFound`.
 
 ## [v0.17.0] (beta) - 2023-12-11
 
diff --git a/src/internal/m365/collection/exchange/restore.go b/src/internal/m365/collection/exchange/restore.go
index 20644962a..dc8395f19 100644
--- a/src/internal/m365/collection/exchange/restore.go
+++ b/src/internal/m365/collection/exchange/restore.go
@@ -4,8 +4,10 @@ import (
 	"bytes"
 	"context"
 	"runtime/trace"
+	"time"
 
 	"github.com/alcionai/clues"
+	"github.com/cenkalti/backoff/v4"
 	"github.com/microsoftgraph/msgraph-sdk-go/models"
 
 	"github.com/alcionai/corso/src/internal/common/ptr"
@@ -213,6 +215,14 @@ func getOrPopulateContainer(
 	return folderID, nil
 }
 
+const (
+	maxRetries          = 3
+	retryInterval       = 750 * time.Millisecond
+	retryMultiplier     = 2
+	retryMaxInterval    = 5 * time.Second
+	retryMaxElapsedTime = 0
+)
+
 func uploadAttachments(
 	ctx context.Context,
 	ap attachmentPoster,
@@ -222,18 +232,57 @@ func uploadAttachments(
 ) error {
 	el := errs.Local()
 
-	for _, a := range as {
+	// Manual testing showed that even small delays between retries could get us
+	// past the issues. Use an exponential backoff that will allow us to keep
+	// runtimes low if there's just one failure for a given attachment but still
+	// waits a reasonable amount of time if there's multiple failures.
+	retryBackoff := backoff.NewExponentialBackOff()
+	retryBackoff.InitialInterval = retryInterval
+	retryBackoff.Multiplier = retryMultiplier
+	retryBackoff.MaxInterval = retryMaxInterval
+	retryBackoff.MaxElapsedTime = retryMaxElapsedTime
+
+	for i, a := range as {
 		if el.Failure() != nil {
 			return el.Failure()
 		}
 
-		err := uploadAttachment(
-			ctx,
-			ap,
-			resourceID,
-			destinationID,
-			itemID,
-			a)
+		actx := clues.Add(ctx, "attachment_num", i)
+
+		var (
+			retry int
+			err   error
+		)
+
+		retryBackoff.Reset()
+
+		for (retry == 0 || graph.IsErrItemNotFound(err)) && retry <= maxRetries {
+			retry++
+
+			ictx := clues.Add(actx, "attempt_num", retry)
+
+			err = uploadAttachment(
+				ictx,
+				ap,
+				resourceID,
+				destinationID,
+				itemID,
+				a)
+
+			// Sometimes graph returns a 404 when we try to post the attachment.
+			// We're not sure why, but maybe it has to do with attaching many items.
+			// In any case, wait a little while and try again.
+			if graph.IsErrItemNotFound(err) && retry <= maxRetries {
+				waitTime := retryBackoff.NextBackOff()
+
+				logger.Ctx(ictx).Infow(
+					"error uploading attachment, retrying",
+					"retry_after", waitTime)
+
+				time.Sleep(waitTime)
+			}
+		}
+
 		if err != nil {
 			// FIXME: I don't know why we're swallowing this error case.
 			// It needs investigation: https://github.com/alcionai/corso/issues/3498
@@ -247,7 +296,7 @@ func uploadAttachments(
 				continue
 			}
 
-			el.AddRecoverable(ctx, clues.WrapWC(ctx, err, "uploading mail attachment"))
+			el.AddRecoverable(actx, clues.WrapWC(ctx, err, "uploading mail attachment"))
 		}
 	}
 
diff --git a/src/pkg/services/m365/api/graph/errors.go b/src/pkg/services/m365/api/graph/errors.go
index b36c544e6..6cc155841 100644
--- a/src/pkg/services/m365/api/graph/errors.go
+++ b/src/pkg/services/m365/api/graph/errors.go
@@ -166,7 +166,7 @@ func IsErrDeletedInFlight(err error) bool {
 }
 
 func IsErrItemNotFound(err error) bool {
-	return hasErrorCode(err, itemNotFound)
+	return hasErrorCode(err, itemNotFound, errorItemNotFound)
 }
 
 func IsErrInvalidDelta(err error) bool {
diff --git a/src/pkg/services/m365/api/graph/errors_test.go b/src/pkg/services/m365/api/graph/errors_test.go
index 8d3c5c5eb..6fc4ead43 100644
--- a/src/pkg/services/m365/api/graph/errors_test.go
+++ b/src/pkg/services/m365/api/graph/errors_test.go
@@ -858,10 +858,15 @@ func (suite *GraphErrorsUnitSuite) TestIsErrItemNotFound() {
 			expect: assert.False,
 		},
 		{
-			name:   "item nott found oDataErr",
+			name:   "item not found oDataErr",
 			err:    graphTD.ODataErr(string(itemNotFound)),
 			expect: assert.True,
 		},
+		{
+			name:   "error item not found oDataErr",
+			err:    graphTD.ODataErr(string(errorItemNotFound)),
+			expect: assert.True,
+		},
 	}
 	for _, test := range table {
 		suite.Run(test.name, func() {