diff --git a/tests/e2e/postgres/allow_missing_test.go b/tests/e2e/postgres/allow_missing_test.go
index 2e61d8eb0..26fa05a1e 100644
--- a/tests/e2e/postgres/allow_missing_test.go
+++ b/tests/e2e/postgres/allow_missing_test.go
@@ -40,8 +40,8 @@ func TestNotAllowMissing(t *testing.T) {
 	// detected.
 	_, err = te.provider.Up(ctx)
 	check.HasError(t, err)
-	// found 1 missing migration: 6
-	check.Contains(t, err.Error(), "missing migration")
+	// found 1 missing (out-of-order) migration: [00006_f.sql]
+	check.Contains(t, err.Error(), "missing (out-of-order) migration")
 	// Confirm db version is unchanged.
 	current, err = te.provider.GetDBVersion(ctx)
 	check.NoError(t, err)
@@ -49,8 +49,8 @@ func TestNotAllowMissing(t *testing.T) {
 
 	_, err = te.provider.UpByOne(ctx)
 	check.HasError(t, err)
-	// found 1 missing migration: 6
-	check.Contains(t, err.Error(), "missing migration")
+	// found 1 missing (out-of-order) migration: [00006_f.sql]
+	check.Contains(t, err.Error(), "missing (out-of-order) migration")
 	// Confirm db version is unchanged.
 	current, err = te.provider.GetDBVersion(ctx)
 	check.NoError(t, err)
@@ -58,8 +58,8 @@ func TestNotAllowMissing(t *testing.T) {
 
 	_, err = te.provider.UpTo(ctx, math.MaxInt64)
 	check.HasError(t, err)
-	// found 1 missing migration: 6
-	check.Contains(t, err.Error(), "missing migration")
+	// found 1 missing (out-of-order) migration: [00006_f.sql]
+	check.Contains(t, err.Error(), "missing (out-of-order) migration")
 	// Confirm db version is unchanged.
 	current, err = te.provider.GetDBVersion(ctx)
 	check.NoError(t, err)
@@ -303,3 +303,42 @@ func TestMigrateAllowMissingDown(t *testing.T) {
 		}
 	}
 }
+
+func TestWithWithoutAllowMissing(t *testing.T) {
+	t.Parallel()
+	ctx := context.Background()
+	// Test for https://github.com/pressly/goose/issues/521
+
+	// Apply 1,2,4,3 then run up without allow missing. If the next requested migration is
+	// 4 then it should not raise an error because it has already been applied.
+	// If goose attempts to apply 4 again then it will raise an error (SQLSTATE 42701) because it
+	// has already been applied. Specifically it will raise a  error.
+	// Create and apply first 5 migrations.
+	opt := goose.DefaultOptions().
+		SetAllowMissing(true)
+	te := newTestEnv(t, migrationsDir, &opt)
+	_, err := te.provider.UpTo(ctx, 2)
+	check.NoError(t, err)
+	_, err = te.provider.ApplyVersion(ctx, 4, true)
+	check.NoError(t, err)
+	res, err := te.provider.UpTo(ctx, 4)
+	check.NoError(t, err)
+	check.Number(t, len(res), 1)
+	check.Number(t, res[0].Version, 3)
+
+	{
+		// Create a new goose provider WITHOUT allow missing, and attempt to apply migration 4.
+		opt := goose.DefaultOptions().
+			SetDir(migrationsDir).
+			SetVerbose(testing.Verbose())
+		provider, err := goose.NewProvider(goose.DialectPostgres, te.db, opt)
+		check.NoError(t, err)
+		results, err := provider.UpTo(ctx, 4)
+		check.NoError(t, err)
+		check.Number(t, len(results), 0)
+		// And now try to apply the next migration in the sequence.
+		result, err := provider.UpByOne(ctx)
+		check.NoError(t, err)
+		check.Number(t, result.Version, 5)
+	}
+}
diff --git a/up.go b/up.go
index 558f1271d..6e91b2e38 100644
--- a/up.go
+++ b/up.go
@@ -5,8 +5,8 @@ import (
 	"errors"
 	"fmt"
 	"math"
+	"path/filepath"
 	"sort"
-	"strconv"
 	"strings"
 
 	"github.com/pressly/goose/v4/internal/dialectadapter"
@@ -92,20 +92,20 @@ func (p *Provider) up(ctx context.Context, upByOne bool, version int64) (_ []*Mi
 	if len(missingMigrations) > 0 && !p.opt.AllowMissing {
 		var collected []string
 		for _, v := range missingMigrations {
-			collected = append(collected, strconv.FormatInt(v, 10))
+			collected = append(collected, v.filename)
 		}
 		msg := "migration"
 		if len(collected) > 1 {
 			msg += "s"
 		}
-		return nil, fmt.Errorf("found %d missing %s: %s",
+		return nil, fmt.Errorf("found %d missing (out-of-order) %s: [%s]",
 			len(missingMigrations), msg, strings.Join(collected, ","))
 	}
 
 	var migrationsToApply []*migration.Migration
 	if p.opt.AllowMissing {
 		for _, v := range missingMigrations {
-			m, err := p.getMigration(v)
+			m, err := p.getMigration(v.versionID)
 			if err != nil {
 				return nil, err
 			}
@@ -133,12 +133,17 @@ func (p *Provider) up(ctx context.Context, upByOne bool, version int64) (_ []*Mi
 	return p.runMigrations(ctx, conn, migrationsToApply, sqlparser.DirectionUp, upByOne)
 }
 
+type missingMigration struct {
+	versionID int64
+	filename  string
+}
+
 // findMissingMigrations returns a list of migrations that are missing from the database. A missing
 // migration is one that has a version less than the max version in the database.
 func findMissingMigrations(
 	dbMigrations []*dialectadapter.ListMigrationsResult,
 	fsMigrations []*migration.Migration,
-) []int64 {
+) []missingMigration {
 	existing := make(map[int64]bool)
 	var max int64
 	for _, m := range dbMigrations {
@@ -147,14 +152,17 @@ func findMissingMigrations(
 			max = m.Version
 		}
 	}
-	var missing []int64
+	var missing []missingMigration
 	for _, m := range fsMigrations {
 		if !existing[m.Version] && m.Version < max {
-			missing = append(missing, m.Version)
+			missing = append(missing, missingMigration{
+				versionID: m.Version,
+				filename:  filepath.Base(m.Fullpath),
+			})
 		}
 	}
 	sort.Slice(missing, func(i, j int) bool {
-		return missing[i] < missing[j]
+		return missing[i].versionID < missing[j].versionID
 	})
 	return missing
 }
diff --git a/up_test.go b/up_test.go
index a95f1b96f..8ff610050 100644
--- a/up_test.go
+++ b/up_test.go
@@ -34,8 +34,8 @@ func TestFindMissingMigrations(t *testing.T) {
 	}
 	got := findMissingMigrations(dbMigrations, fsMigrations)
 	check.Number(t, len(got), 2)
-	check.Number(t, got[0], 2)
-	check.Number(t, got[1], 6)
+	check.Number(t, got[0].versionID, 2)
+	check.Number(t, got[1].versionID, 6)
 
 	// Sanity check.
 	check.Number(t, len(findMissingMigrations(nil, nil)), 0)