diff --git a/CHANGES.md b/CHANGES.md
index 79d2fe2e1..657ca1920 100644
--- a/CHANGES.md
+++ b/CHANGES.md
@@ -1,5 +1,26 @@
 # Changelog
 
+## Dendrite 0.9.9 (2022-09-22)
+
+### Features
+
+* Dendrite will now try to keep HTTP connections open to remote federated servers for a few minutes after a request and attempt to reuse those connections where possible
+  * This should reduce the amount of time spent on TLS handshakes and often speed up requests to remote servers
+  * This new behaviour can be disabled with the `federation_api.disable_http_keepalives` option if needed
+* A number of dependencies have been updated
+
+### Fixes
+
+* A bug where the roomserver did not correctly propagate rewritten room state to downstream components (like the federation API and sync API) has been fixed, which could cause issues when performing a federated join to a previously left room
+* Event auth now correctly parses the `join_authorised_via_users_server` field in the membership event content
+* Database migrations should no longer produce unique constraint errors at Dendrite startup
+* The `origin` of device list updates should now be populated correctly
+* Send-to-device messages will no longer be dropped if we fail to publish them to specific devices
+* The roomserver query to find state after events will now always resolve state if there are multiple prev events
+* The roomserver will now return no memberships if querying history visibility for an event which has no state snapshot
+* The device list updater will now mark a device list as stale if a requesting device ID is not known
+* Transactions sent to appservices should no longer have accidental duplicated transaction IDs (contributed by [tak-hntlabs](https://github.com/tak-hntlabs))
+
 ## Dendrite 0.9.8 (2022-09-12)
 
 ### Important
diff --git a/cmd/dendrite-demo-pinecone/main.go b/cmd/dendrite-demo-pinecone/main.go
index 99e597e59..da63f9a2c 100644
--- a/cmd/dendrite-demo-pinecone/main.go
+++ b/cmd/dendrite-demo-pinecone/main.go
@@ -24,6 +24,7 @@ import (
 	"net"
 	"net/http"
 	"os"
+	"path/filepath"
 	"strings"
 	"time"
 
@@ -62,6 +63,7 @@ var (
 	instancePort   = flag.Int("port", 8008, "the port that the client API will listen on")
 	instancePeer   = flag.String("peer", "", "the static Pinecone peers to connect to, comma separated-list")
 	instanceListen = flag.String("listen", ":0", "the port Pinecone peers can connect to")
+	instanceDir    = flag.String("dir", ".", "the directory to store the databases in (if --config not specified)")
 )
 
 // nolint:gocyclo
@@ -88,7 +90,7 @@ func main() {
 		cfg = setup.ParseFlags(true)
 		sk = cfg.Global.PrivateKey
 	} else {
-		keyfile := *instanceName + ".pem"
+		keyfile := filepath.Join(*instanceDir, *instanceName) + ".pem"
 		if _, err := os.Stat(keyfile); os.IsNotExist(err) {
 			oldkeyfile := *instanceName + ".key"
 			if _, err = os.Stat(oldkeyfile); os.IsNotExist(err) {
@@ -129,15 +131,15 @@ func main() {
 			Monolithic: true,
 		})
 		cfg.Global.PrivateKey = sk
-		cfg.Global.JetStream.StoragePath = config.Path(fmt.Sprintf("%s/", *instanceName))
-		cfg.UserAPI.AccountDatabase.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-account.db", *instanceName))
-		cfg.MediaAPI.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-mediaapi.db", *instanceName))
-		cfg.SyncAPI.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-syncapi.db", *instanceName))
-		cfg.RoomServer.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-roomserver.db", *instanceName))
-		cfg.KeyServer.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-keyserver.db", *instanceName))
-		cfg.FederationAPI.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-federationapi.db", *instanceName))
+		cfg.Global.JetStream.StoragePath = config.Path(fmt.Sprintf("%s/", filepath.Join(*instanceDir, *instanceName)))
+		cfg.UserAPI.AccountDatabase.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-account.db", filepath.Join(*instanceDir, *instanceName)))
+		cfg.MediaAPI.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-mediaapi.db", filepath.Join(*instanceDir, *instanceName)))
+		cfg.SyncAPI.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-syncapi.db", filepath.Join(*instanceDir, *instanceName)))
+		cfg.RoomServer.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-roomserver.db", filepath.Join(*instanceDir, *instanceName)))
+		cfg.KeyServer.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-keyserver.db", filepath.Join(*instanceDir, *instanceName)))
+		cfg.FederationAPI.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-federationapi.db", filepath.Join(*instanceDir, *instanceName)))
 		cfg.MSCs.MSCs = []string{"msc2836", "msc2946"}
-		cfg.MSCs.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-mscs.db", *instanceName))
+		cfg.MSCs.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-mscs.db", filepath.Join(*instanceDir, *instanceName)))
 		cfg.ClientAPI.RegistrationDisabled = false
 		cfg.ClientAPI.OpenRegistrationWithoutVerificationEnabled = true
 		if err := cfg.Derive(); err != nil {
diff --git a/cmd/dendrite-demo-yggdrasil/main.go b/cmd/dendrite-demo-yggdrasil/main.go
index 868d9826a..cd0066679 100644
--- a/cmd/dendrite-demo-yggdrasil/main.go
+++ b/cmd/dendrite-demo-yggdrasil/main.go
@@ -24,6 +24,7 @@ import (
 	"net"
 	"net/http"
 	"os"
+	"path/filepath"
 	"time"
 
 	"github.com/matrix-org/gomatrixserverlib"
@@ -56,6 +57,7 @@ var (
 	instancePort   = flag.Int("port", 8008, "the port that the client API will listen on")
 	instancePeer   = flag.String("peer", "", "the static Yggdrasil peers to connect to, comma separated-list")
 	instanceListen = flag.String("listen", "tcp://:0", "the port Yggdrasil peers can connect to")
+	instanceDir    = flag.String("dir", ".", "the directory to store the databases in (if --config not specified)")
 )
 
 func main() {
@@ -76,7 +78,7 @@ func main() {
 
 	cfg := &config.Dendrite{}
 
-	keyfile := *instanceName + ".pem"
+	keyfile := filepath.Join(*instanceDir, *instanceName) + ".pem"
 	if _, err := os.Stat(keyfile); os.IsNotExist(err) {
 		oldkeyfile := *instanceName + ".key"
 		if _, err = os.Stat(oldkeyfile); os.IsNotExist(err) {
@@ -121,15 +123,15 @@ func main() {
 			Monolithic: true,
 		})
 		cfg.Global.PrivateKey = sk
-		cfg.Global.JetStream.StoragePath = config.Path(fmt.Sprintf("%s/", *instanceName))
-		cfg.UserAPI.AccountDatabase.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-account.db", *instanceName))
-		cfg.MediaAPI.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-mediaapi.db", *instanceName))
-		cfg.SyncAPI.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-syncapi.db", *instanceName))
-		cfg.RoomServer.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-roomserver.db", *instanceName))
-		cfg.KeyServer.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-keyserver.db", *instanceName))
-		cfg.FederationAPI.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-federationapi.db", *instanceName))
-		cfg.MSCs.MSCs = []string{"msc2836"}
-		cfg.MSCs.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-mscs.db", *instanceName))
+		cfg.Global.JetStream.StoragePath = config.Path(filepath.Join(*instanceDir, *instanceName))
+		cfg.UserAPI.AccountDatabase.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-account.db", filepath.Join(*instanceDir, *instanceName)))
+		cfg.MediaAPI.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-mediaapi.db", filepath.Join(*instanceDir, *instanceName)))
+		cfg.SyncAPI.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-syncapi.db", filepath.Join(*instanceDir, *instanceName)))
+		cfg.RoomServer.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-roomserver.db", filepath.Join(*instanceDir, *instanceName)))
+		cfg.KeyServer.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-keyserver.db", filepath.Join(*instanceDir, *instanceName)))
+		cfg.FederationAPI.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-federationapi.db", filepath.Join(*instanceDir, *instanceName)))
+		cfg.MSCs.MSCs = []string{"msc2836", "msc2946"}
+		cfg.MSCs.Database.ConnectionString = config.DataSource(fmt.Sprintf("file:%s-mscs.db", filepath.Join(*instanceDir, *instanceName)))
 		cfg.ClientAPI.RegistrationDisabled = false
 		cfg.ClientAPI.OpenRegistrationWithoutVerificationEnabled = true
 		if err := cfg.Derive(); err != nil {
diff --git a/docs/Gemfile.lock b/docs/Gemfile.lock
index 88d33ae84..bc73df728 100644
--- a/docs/Gemfile.lock
+++ b/docs/Gemfile.lock
@@ -14,7 +14,7 @@ GEM
       execjs
     coffee-script-source (1.11.1)
     colorator (1.1.0)
-    commonmarker (0.23.4)
+    commonmarker (0.23.6)
     concurrent-ruby (1.1.10)
     dnsruby (1.61.9)
       simpleidn (~> 0.1)
diff --git a/federationapi/federationapi_keys_test.go b/federationapi/federationapi_keys_test.go
index 4469da35b..85cc43aa5 100644
--- a/federationapi/federationapi_keys_test.go
+++ b/federationapi/federationapi_keys_test.go
@@ -12,12 +12,13 @@ import (
 	"testing"
 	"time"
 
+	"github.com/matrix-org/gomatrixserverlib"
+
 	"github.com/matrix-org/dendrite/federationapi/api"
 	"github.com/matrix-org/dendrite/federationapi/routing"
 	"github.com/matrix-org/dendrite/internal/caching"
 	"github.com/matrix-org/dendrite/setup/base"
 	"github.com/matrix-org/dendrite/setup/config"
-	"github.com/matrix-org/gomatrixserverlib"
 )
 
 type server struct {
@@ -86,7 +87,12 @@ func TestMain(m *testing.M) {
 			cfg.Global.JetStream.StoragePath = config.Path(d)
 			cfg.Global.KeyID = serverKeyID
 			cfg.Global.KeyValidityPeriod = s.validity
-			cfg.FederationAPI.Database.ConnectionString = config.DataSource("file::memory:")
+			f, err := os.CreateTemp(d, "federation_keys_test*.db")
+			if err != nil {
+				return -1
+			}
+			defer f.Close()
+			cfg.FederationAPI.Database.ConnectionString = config.DataSource("file:" + f.Name())
 			s.config = &cfg.FederationAPI
 
 			// Create a transport which redirects federation requests to
diff --git a/federationapi/federationapi_test.go b/federationapi/federationapi_test.go
index 15f7a6840..e923143a7 100644
--- a/federationapi/federationapi_test.go
+++ b/federationapi/federationapi_test.go
@@ -10,6 +10,10 @@ import (
 	"testing"
 	"time"
 
+	"github.com/matrix-org/gomatrix"
+	"github.com/matrix-org/gomatrixserverlib"
+	"github.com/nats-io/nats.go"
+
 	"github.com/matrix-org/dendrite/federationapi"
 	"github.com/matrix-org/dendrite/federationapi/api"
 	"github.com/matrix-org/dendrite/federationapi/internal"
@@ -20,9 +24,6 @@ import (
 	"github.com/matrix-org/dendrite/setup/jetstream"
 	"github.com/matrix-org/dendrite/test"
 	"github.com/matrix-org/dendrite/test/testrig"
-	"github.com/matrix-org/gomatrix"
-	"github.com/matrix-org/gomatrixserverlib"
-	"github.com/nats-io/nats.go"
 )
 
 type fedRoomserverAPI struct {
@@ -271,7 +272,6 @@ func TestRoomsV3URLEscapeDoNot404(t *testing.T) {
 	cfg.Global.ServerName = gomatrixserverlib.ServerName("localhost")
 	cfg.Global.PrivateKey = privKey
 	cfg.Global.JetStream.InMemory = true
-	cfg.FederationAPI.Database.ConnectionString = config.DataSource("file::memory:")
 	base := base.NewBaseDendrite(cfg, "Monolith")
 	keyRing := &test.NopJSONVerifier{}
 	// TODO: This is pretty fragile, as if anything calls anything on these nils this test will break.
diff --git a/go.mod b/go.mod
index 15e23d4f0..1a551aef7 100644
--- a/go.mod
+++ b/go.mod
@@ -22,11 +22,11 @@ require (
 	github.com/matrix-org/dugong v0.0.0-20210921133753-66e6b1c67e2e
 	github.com/matrix-org/go-sqlite3-js v0.0.0-20220419092513-28aa791a1c91
 	github.com/matrix-org/gomatrix v0.0.0-20210324163249-be2af5ef2e16
-	github.com/matrix-org/gomatrixserverlib v0.0.0-20220920133029-eb0633c739ef
-	github.com/matrix-org/pinecone v0.0.0-20220915154206-df85cb5026fc
+	github.com/matrix-org/gomatrixserverlib v0.0.0-20220923115829-2217f6c65ce3
+	github.com/matrix-org/pinecone v0.0.0-20220923151905-0900fceecb89
 	github.com/matrix-org/util v0.0.0-20200807132607-55161520e1d4
 	github.com/mattn/go-sqlite3 v1.14.15
-	github.com/nats-io/nats-server/v2 v2.9.0
+	github.com/nats-io/nats-server/v2 v2.9.1-0.20220920152220-52d7b481c4b5
 	github.com/nats-io/nats.go v1.17.0
 	github.com/neilalexander/utp v0.1.1-0.20210727203401-54ae7b1cd5f9
 	github.com/nfnt/resize v0.0.0-20180221191011-83c6a9932646
diff --git a/go.sum b/go.sum
index 4bffea59f..183f7f1a4 100644
--- a/go.sum
+++ b/go.sum
@@ -409,10 +409,10 @@ github.com/matrix-org/go-sqlite3-js v0.0.0-20220419092513-28aa791a1c91 h1:s7fexw
 github.com/matrix-org/go-sqlite3-js v0.0.0-20220419092513-28aa791a1c91/go.mod h1:e+cg2q7C7yE5QnAXgzo512tgFh1RbQLC0+jozuegKgo=
 github.com/matrix-org/gomatrix v0.0.0-20210324163249-be2af5ef2e16 h1:ZtO5uywdd5dLDCud4r0r55eP4j9FuUNpl60Gmntcop4=
 github.com/matrix-org/gomatrix v0.0.0-20210324163249-be2af5ef2e16/go.mod h1:/gBX06Kw0exX1HrwmoBibFA98yBk/jxKpGVeyQbff+s=
-github.com/matrix-org/gomatrixserverlib v0.0.0-20220920133029-eb0633c739ef h1:qnDDZVkqKAB8if91AUX2VtQGCGnxLBYYt2tG972SYPk=
-github.com/matrix-org/gomatrixserverlib v0.0.0-20220920133029-eb0633c739ef/go.mod h1:Mtifyr8q8htcBeugvlDnkBcNUy5LO8OzUoplAf1+mb4=
-github.com/matrix-org/pinecone v0.0.0-20220915154206-df85cb5026fc h1:NAf6Xec/RoYD+/UT3m2q58yZAu0pYA9C4gc/RbS89ls=
-github.com/matrix-org/pinecone v0.0.0-20220915154206-df85cb5026fc/go.mod h1:K0N1ixHQxXoCyqolDqVxPM3ArrDtcMs8yegOx2Lfv9k=
+github.com/matrix-org/gomatrixserverlib v0.0.0-20220923115829-2217f6c65ce3 h1:u3FKZmXxfhv3XhD8RziBlt96QTt8eHFhg1upCloBh2g=
+github.com/matrix-org/gomatrixserverlib v0.0.0-20220923115829-2217f6c65ce3/go.mod h1:Mtifyr8q8htcBeugvlDnkBcNUy5LO8OzUoplAf1+mb4=
+github.com/matrix-org/pinecone v0.0.0-20220923151905-0900fceecb89 h1:Ym50Fgn3GiYya4p29k3nJ5nYsalFGev3eIm3DeGNIq4=
+github.com/matrix-org/pinecone v0.0.0-20220923151905-0900fceecb89/go.mod h1:K0N1ixHQxXoCyqolDqVxPM3ArrDtcMs8yegOx2Lfv9k=
 github.com/matrix-org/util v0.0.0-20200807132607-55161520e1d4 h1:eCEHXWDv9Rm335MSuB49mFUK44bwZPFSDde3ORE3syk=
 github.com/matrix-org/util v0.0.0-20200807132607-55161520e1d4/go.mod h1:vVQlW/emklohkZnOPwD3LrZUBqdfsbiyO3p1lNV8F6U=
 github.com/mattn/go-isatty v0.0.12/go.mod h1:cbi8OIDigv2wuxKPP5vlRcQ1OAZbq2CE4Kysco4FUpU=
@@ -448,8 +448,8 @@ github.com/mwitkow/go-conntrack v0.0.0-20161129095857-cc309e4a2223/go.mod h1:qRW
 github.com/mwitkow/go-conntrack v0.0.0-20190716064945-2f068394615f/go.mod h1:qRWi+5nqEBWmkhHvq77mSJWrCKwh8bxhgT7d/eI7P4U=
 github.com/nats-io/jwt/v2 v2.3.0 h1:z2mA1a7tIf5ShggOFlR1oBPgd6hGqcDYsISxZByUzdI=
 github.com/nats-io/jwt/v2 v2.3.0/go.mod h1:0tqz9Hlu6bCBFLWAASKhE5vUA4c24L9KPUUgvwumE/k=
-github.com/nats-io/nats-server/v2 v2.9.0 h1:DLWu+7/VgGOoChcDKytnUZPAmudpv7o/MhKmNrnH1RE=
-github.com/nats-io/nats-server/v2 v2.9.0/go.mod h1:BWKY6217RvhI+FDoOLZ2BH+hOC37xeKRBlQ1Lz7teKI=
+github.com/nats-io/nats-server/v2 v2.9.1-0.20220920152220-52d7b481c4b5 h1:G/YGSXcJ2bUofD8Ts49it4VNezaJLQldI6fZR+wIUts=
+github.com/nats-io/nats-server/v2 v2.9.1-0.20220920152220-52d7b481c4b5/go.mod h1:BWKY6217RvhI+FDoOLZ2BH+hOC37xeKRBlQ1Lz7teKI=
 github.com/nats-io/nats.go v1.17.0 h1:1jp5BThsdGlN91hW0k3YEfJbfACjiOYtUiLXG0RL4IE=
 github.com/nats-io/nats.go v1.17.0/go.mod h1:BPko4oXsySz4aSWeFgOHLZs3G4Jq4ZAyE6/zMCxRT6w=
 github.com/nats-io/nkeys v0.3.0 h1:cgM5tL53EvYRU+2YLXIK0G2mJtK12Ft9oeooSZMA2G8=
diff --git a/internal/sqlutil/migrate.go b/internal/sqlutil/migrate.go
index b6a8b1f25..a66a75826 100644
--- a/internal/sqlutil/migrate.go
+++ b/internal/sqlutil/migrate.go
@@ -49,12 +49,13 @@ type Migration struct {
 	Down func(ctx context.Context, txn *sql.Tx) error
 }
 
-// Migrator
+// Migrator contains fields required to run migrations.
 type Migrator struct {
 	db              *sql.DB
 	migrations      []Migration
 	knownMigrations map[string]struct{}
 	mutex           *sync.Mutex
+	insertStmt      *sql.Stmt
 }
 
 // NewMigrator creates a new DB migrator.
@@ -82,35 +83,26 @@ func (m *Migrator) AddMigrations(migrations ...Migration) {
 
 // Up executes all migrations in order they were added.
 func (m *Migrator) Up(ctx context.Context) error {
-	var (
-		err             error
-		dendriteVersion = internal.VersionString()
-	)
 	// ensure there is a table for known migrations
 	executedMigrations, err := m.ExecutedMigrations(ctx)
 	if err != nil {
 		return fmt.Errorf("unable to create/get migrations: %w", err)
 	}
-
+	// ensure we close the insert statement, as it's not needed anymore
+	defer m.close()
 	return WithTransaction(m.db, func(txn *sql.Tx) error {
 		for i := range m.migrations {
-			now := time.Now().UTC().Format(time.RFC3339)
 			migration := m.migrations[i]
 			// Skip migration if it was already executed
 			if _, ok := executedMigrations[migration.Version]; ok {
 				continue
 			}
 			logrus.Debugf("Executing database migration '%s'", migration.Version)
-			err = migration.Up(ctx, txn)
-			if err != nil {
+
+			if err = migration.Up(ctx, txn); err != nil {
 				return fmt.Errorf("unable to execute migration '%s': %w", migration.Version, err)
 			}
-			_, err = txn.ExecContext(ctx, insertVersionSQL,
-				migration.Version,
-				now,
-				dendriteVersion,
-			)
-			if err != nil {
+			if err = m.insertMigration(ctx, txn, migration.Version); err != nil {
 				return fmt.Errorf("unable to insert executed migrations: %w", err)
 			}
 		}
@@ -118,6 +110,23 @@ func (m *Migrator) Up(ctx context.Context) error {
 	})
 }
 
+func (m *Migrator) insertMigration(ctx context.Context, txn *sql.Tx, migrationName string) error {
+	if m.insertStmt == nil {
+		stmt, err := m.db.Prepare(insertVersionSQL)
+		if err != nil {
+			return fmt.Errorf("unable to prepare insert statement: %w", err)
+		}
+		m.insertStmt = stmt
+	}
+	stmt := TxStmtContext(ctx, txn, m.insertStmt)
+	_, err := stmt.ExecContext(ctx,
+		migrationName,
+		time.Now().Format(time.RFC3339),
+		internal.VersionString(),
+	)
+	return err
+}
+
 // ExecutedMigrations returns a map with already executed migrations in addition to creating the
 // migrations table, if it doesn't exist.
 func (m *Migrator) ExecutedMigrations(ctx context.Context) (map[string]struct{}, error) {
@@ -146,19 +155,20 @@ func (m *Migrator) ExecutedMigrations(ctx context.Context) (map[string]struct{},
 // inserts a migration given their name to the database.
 // This should only be used when manually inserting migrations.
 func InsertMigration(ctx context.Context, db *sql.DB, migrationName string) error {
-	_, err := db.ExecContext(ctx, createDBMigrationsSQL)
+	m := NewMigrator(db)
+	defer m.close()
+	existingMigrations, err := m.ExecutedMigrations(ctx)
 	if err != nil {
-		return fmt.Errorf("unable to create db_migrations: %w", err)
+		return err
 	}
-	_, err = db.ExecContext(ctx, insertVersionSQL,
-		migrationName,
-		time.Now().Format(time.RFC3339),
-		internal.VersionString(),
-	)
-	// If the migration was already executed, we'll get a unique constraint error,
-	// return nil instead, to avoid unnecessary logging.
-	if IsUniqueConstraintViolationErr(err) {
+	if _, ok := existingMigrations[migrationName]; ok {
 		return nil
 	}
-	return err
+	return m.insertMigration(ctx, nil, migrationName)
+}
+
+func (m *Migrator) close() {
+	if m.insertStmt != nil {
+		internal.CloseAndLogIfError(context.Background(), m.insertStmt, "unable to close insert statement")
+	}
 }
diff --git a/internal/sqlutil/migrate_test.go b/internal/sqlutil/migrate_test.go
index d8bcae196..5116237a1 100644
--- a/internal/sqlutil/migrate_test.go
+++ b/internal/sqlutil/migrate_test.go
@@ -7,9 +7,10 @@ import (
 	"reflect"
 	"testing"
 
+	_ "github.com/mattn/go-sqlite3"
+
 	"github.com/matrix-org/dendrite/internal/sqlutil"
 	"github.com/matrix-org/dendrite/test"
-	_ "github.com/mattn/go-sqlite3"
 )
 
 var dummyMigrations = []sqlutil.Migration{
@@ -81,11 +82,12 @@ func Test_migrations_Up(t *testing.T) {
 	}
 
 	ctx := context.Background()
-	for _, tt := range tests {
-		t.Run(tt.name, func(t *testing.T) {
-			test.WithAllDatabases(t, func(t *testing.T, dbType test.DBType) {
-				conStr, close := test.PrepareDBConnectionString(t, dbType)
-				defer close()
+	test.WithAllDatabases(t, func(t *testing.T, dbType test.DBType) {
+		conStr, close := test.PrepareDBConnectionString(t, dbType)
+		defer close()
+
+		for _, tt := range tests {
+			t.Run(tt.name, func(t *testing.T) {
 				driverName := "sqlite3"
 				if dbType == test.DBTypePostgres {
 					driverName = "postgres"
@@ -107,6 +109,30 @@ func Test_migrations_Up(t *testing.T) {
 					t.Errorf("expected: %+v, got %v", tt.wantResult, result)
 				}
 			})
-		})
-	}
+		}
+	})
+}
+
+func Test_insertMigration(t *testing.T) {
+	test.WithAllDatabases(t, func(t *testing.T, dbType test.DBType) {
+		conStr, close := test.PrepareDBConnectionString(t, dbType)
+		defer close()
+		driverName := "sqlite3"
+		if dbType == test.DBTypePostgres {
+			driverName = "postgres"
+		}
+
+		db, err := sql.Open(driverName, conStr)
+		if err != nil {
+			t.Errorf("unable to open database: %v", err)
+		}
+
+		if err := sqlutil.InsertMigration(context.Background(), db, "testing"); err != nil {
+			t.Fatalf("unable to insert migration: %s", err)
+		}
+		// Second insert should not return an error, as it was already executed.
+		if err := sqlutil.InsertMigration(context.Background(), db, "testing"); err != nil {
+			t.Fatalf("unable to insert migration: %s", err)
+		}
+	})
 }
diff --git a/internal/version.go b/internal/version.go
index ef7b879c2..f9b101702 100644
--- a/internal/version.go
+++ b/internal/version.go
@@ -17,7 +17,7 @@ var build string
 const (
 	VersionMajor = 0
 	VersionMinor = 9
-	VersionPatch = 8
+	VersionPatch = 9
 	VersionTag   = "" // example: "rc1"
 )
 
diff --git a/syncapi/sync/requestpool.go b/syncapi/sync/requestpool.go
index c2c9616e8..b2ea105ff 100644
--- a/syncapi/sync/requestpool.go
+++ b/syncapi/sync/requestpool.go
@@ -308,6 +308,12 @@ func (rp *RequestPool) OnIncomingSyncRequest(req *http.Request, device *userapi.
 		if syncReq.Since.IsEmpty() {
 			// Complete sync
 			syncReq.Response.NextBatch = types.StreamingToken{
+				// Get the current DeviceListPosition first, as the currentPosition
+				// might advance while processing other streams, resulting in flakey
+				// tests.
+				DeviceListPosition: rp.streams.DeviceListStreamProvider.CompleteSync(
+					syncReq.Context, syncReq,
+				),
 				PDUPosition: rp.streams.PDUStreamProvider.CompleteSync(
 					syncReq.Context, syncReq,
 				),
@@ -329,9 +335,6 @@ func (rp *RequestPool) OnIncomingSyncRequest(req *http.Request, device *userapi.
 				NotificationDataPosition: rp.streams.NotificationDataStreamProvider.CompleteSync(
 					syncReq.Context, syncReq,
 				),
-				DeviceListPosition: rp.streams.DeviceListStreamProvider.CompleteSync(
-					syncReq.Context, syncReq,
-				),
 				PresencePosition: rp.streams.PresenceStreamProvider.CompleteSync(
 					syncReq.Context, syncReq,
 				),