diff --git a/api/object.go b/api/object.go
index d8336e7f..64baba44 100644
--- a/api/object.go
+++ b/api/object.go
@@ -59,19 +59,20 @@ func (o *ObjectResource) Rel(name string) (*LinkRelation, bool) {
 	return rel, ok
 }
 
-// IsExpired returns true if any of the actions in this object resource have an
-// ExpiresAt field that is after the given instant "now".
+// IsExpired returns true, and the time of the expired action, if any of the
+// actions in this object resource have an ExpiresAt field that is after the
+// given instant "now".
 //
 // If the object contains no actions, or none of the actions it does contain
 // have non-zero ExpiresAt fields, the object is not expired.
-func (o *ObjectResource) IsExpired(now time.Time) bool {
+func (o *ObjectResource) IsExpired(now time.Time) (time.Time, bool) {
 	for _, a := range o.Actions {
 		if !a.ExpiresAt.IsZero() && a.ExpiresAt.Before(now) {
-			return true
+			return a.ExpiresAt, true
 		}
 	}
 
-	return false
+	return time.Time{}, false
 }
 
 func (o *ObjectResource) NeedsAuth() bool {
diff --git a/api/object_test.go b/api/object_test.go
index 9aed52e4..a3e146b8 100644
--- a/api/object_test.go
+++ b/api/object_test.go
@@ -14,7 +14,8 @@ func TestObjectsWithNoActionsAreNotExpired(t *testing.T) {
 		Actions: map[string]*api.LinkRelation{},
 	}
 
-	assert.False(t, o.IsExpired(time.Now()))
+	_, expired := o.IsExpired(time.Now())
+	assert.False(t, expired)
 }
 
 func TestObjectsWithZeroValueTimesAreNotExpired(t *testing.T) {
@@ -28,7 +29,8 @@ func TestObjectsWithZeroValueTimesAreNotExpired(t *testing.T) {
 		},
 	}
 
-	assert.False(t, o.IsExpired(time.Now()))
+	_, expired := o.IsExpired(time.Now())
+	assert.False(t, expired)
 }
 
 func TestObjectsWithExpirationDatesAreExpired(t *testing.T) {
@@ -45,5 +47,7 @@ func TestObjectsWithExpirationDatesAreExpired(t *testing.T) {
 		},
 	}
 
-	assert.True(t, o.IsExpired(now))
+	expiredAt, expired := o.IsExpired(now)
+	assert.Equal(t, expires, expiredAt)
+	assert.True(t, expired)
 }
diff --git a/transfer/adapterbase.go b/transfer/adapterbase.go
index 432c9e94..2b9f6b7f 100644
--- a/transfer/adapterbase.go
+++ b/transfer/adapterbase.go
@@ -124,11 +124,18 @@ func (a *adapterBase) worker(workerNum int, ctx interface{}) {
 		}
 		tracerx.Printf("xfer: adapter %q worker %d processing job for %q", a.Name(), workerNum, t.Object.Oid)
 
+		// tt is the time that we are to compare the transfer's
+		// `expired_at` property against.
+		tt := time.Now().Add(-objectExpirationGracePeriod)
+
 		// Actual transfer happens here
 		var err error
-		if t.Object.IsExpired(time.Now().Add(objectExpirationGracePeriod)) {
+		if expAt, expired := t.Object.IsExpired(tt); expired {
 			tracerx.Printf("xfer: adapter %q worker %d found job for %q expired, retrying...", a.Name(), workerNum, t.Object.Oid)
-			err = errors.NewRetriableError(errors.Errorf("lfs/transfer: object %q has expired", t.Object.Oid))
+			err = errors.NewRetriableError(errors.Errorf(
+				"lfs/transfer: object %q has expired at %s, %s ago",
+				t.Object.Oid, expAt, tt.Sub(expAt),
+			))
 		} else if t.Object.Size < 0 {
 			tracerx.Printf("xfer: adapter %q worker %d found invalid size for %q (got: %d), retrying...", a.Name(), workerNum, t.Object.Oid, t.Object.Size)
 			err = fmt.Errorf("Git LFS: object %q has invalid size (got: %d)", t.Object.Oid, t.Object.Size)