diff --git a/server/handlers/default_test.go b/server/handlers/default_test.go
index 75d1a47fdc..ab6b716be2 100644
--- a/server/handlers/default_test.go
+++ b/server/handlers/default_test.go
@@ -241,12 +241,19 @@ func TestGetHandlerSnapshot(t *testing.T) {
 
 	ctx := getContext(handlerState{store: metaStore, crypto: crypto})
 
+	// Need to create a timestamp and snapshot
 	sn, err := repo.SignSnapshot(data.DefaultExpires("snapshot"))
 	snJSON, err := json.Marshal(sn)
 	require.NoError(t, err)
 	metaStore.UpdateCurrent(
 		"gun", storage.MetaUpdate{Role: "snapshot", Version: 1, Data: snJSON})
 
+	ts, err := repo.SignTimestamp(data.DefaultExpires("timestamp"))
+	tsJSON, err := json.Marshal(ts)
+	require.NoError(t, err)
+	metaStore.UpdateCurrent(
+		"gun", storage.MetaUpdate{Role: "timestamp", Version: 1, Data: tsJSON})
+
 	req := &http.Request{
 		Body: ioutil.NopCloser(bytes.NewBuffer(nil)),
 	}
diff --git a/server/handlers/roles.go b/server/handlers/roles.go
index be2b788c1d..5681c1d47c 100644
--- a/server/handlers/roles.go
+++ b/server/handlers/roles.go
@@ -5,8 +5,11 @@ import (
 
 	"golang.org/x/net/context"
 
+	"encoding/hex"
+	"encoding/json"
+	"fmt"
+	"github.com/docker/notary"
 	"github.com/docker/notary/server/errors"
-	"github.com/docker/notary/server/snapshot"
 	"github.com/docker/notary/server/storage"
 	"github.com/docker/notary/server/timestamp"
 	"github.com/docker/notary/tuf/data"
@@ -61,12 +64,10 @@ func getMaybeServerSigned(ctx context.Context, store storage.MetaStore, gun, rol
 		out          []byte
 		err          error
 	)
-	switch role {
-	case data.CanonicalSnapshotRole:
-		lastModified, out, err = snapshot.GetOrCreateSnapshot(gun, store, cryptoService)
-	case data.CanonicalTimestampRole:
-		lastModified, out, err = timestamp.GetOrCreateTimestamp(gun, store, cryptoService)
+	if role != data.CanonicalTimestampRole && role != data.CanonicalSnapshotRole {
+		return nil, nil, fmt.Errorf("role %s cannot be server signed", role)
 	}
+	lastModified, out, err = timestamp.GetOrCreateTimestamp(gun, store, cryptoService)
 	if err != nil {
 		switch err.(type) {
 		case *storage.ErrNoKey, storage.ErrNotFound:
@@ -76,5 +77,22 @@ func getMaybeServerSigned(ctx context.Context, store storage.MetaStore, gun, rol
 		}
 	}
 
+	// If we wanted the snapshot, get it by checksum from the timestamp data
+	if role == data.CanonicalSnapshotRole {
+		ts := new(data.SignedTimestamp)
+		if err := json.Unmarshal(out, ts); err != nil {
+			return nil, nil, err
+		}
+		snapshotChecksums, err := ts.GetSnapshot()
+		if err != nil || snapshotChecksums == nil {
+			return nil, nil, fmt.Errorf("could not retrieve latest snapshot checksum")
+		}
+		if snapshotSha256Bytes, ok := snapshotChecksums.Hashes[notary.SHA256]; ok {
+			snapshotSha256Hex := hex.EncodeToString(snapshotSha256Bytes[:])
+			return store.GetChecksum(gun, role, snapshotSha256Hex)
+		}
+		return nil, nil, fmt.Errorf("could not retrieve sha256 snapshot checksum")
+	}
+
 	return lastModified, out, nil
 }
diff --git a/server/snapshot/snapshot.go b/server/snapshot/snapshot.go
index f9508bd973..e08f2b086b 100644
--- a/server/snapshot/snapshot.go
+++ b/server/snapshot/snapshot.go
@@ -44,9 +44,11 @@ func GetOrCreateSnapshotKey(gun string, store storage.KeyStore, crypto signed.Cr
 	return nil, err
 }
 
-// GetOrCreateSnapshot either returns the exisiting latest snapshot, or uses
-// whatever the most recent snapshot is to create the next one, only updating
-// the expiry time and version.
+// GetOrCreateSnapshot either returns the existing latest snapshot, or uses
+// whatever the most recent snapshot is to generate the next one, only updating
+// the expiry time and version.  Note that this function does not write generated
+// snapshots to the underlying data store, and will either return the latest snapshot time
+// or nil as the time modified
 func GetOrCreateSnapshot(gun string, store storage.MetaStore, cryptoService signed.CryptoService) (
 	*time.Time, []byte, error) {
 
@@ -85,13 +87,7 @@ func GetOrCreateSnapshot(gun string, store storage.MetaStore, cryptoService sign
 		logrus.Error("Failed to create a new snapshot")
 		return nil, nil, err
 	}
-
-	c := time.Now()
-	if err = store.UpdateCurrent(gun, *snapshotUpdate); err != nil {
-		return nil, nil, err
-	}
-
-	return &c, snapshotUpdate.Data, nil
+	return nil, snapshotUpdate.Data, nil
 }
 
 // snapshotExpired simply checks if the snapshot is past its expiry time
diff --git a/server/storage/rethinkdb.go b/server/storage/rethinkdb.go
index 385162d8eb..78b17144a8 100644
--- a/server/storage/rethinkdb.go
+++ b/server/storage/rethinkdb.go
@@ -4,10 +4,12 @@ import (
 	"crypto/sha256"
 	"encoding/hex"
 	"fmt"
+	"sort"
 	"time"
 
 	"github.com/dancannon/gorethink"
 	"github.com/docker/notary/storage/rethinkdb"
+	"github.com/docker/notary/tuf/data"
 )
 
 // RDBTUFFile is a tuf file record
@@ -19,6 +21,7 @@ type RDBTUFFile struct {
 	Version        int           `gorethink:"version"`
 	Sha256         string        `gorethink:"sha256"`
 	Data           []byte        `gorethink:"data"`
+	TSchecksum     string        `gorethink:"timestamp_checksum"`
 }
 
 // TableName returns the table name for the record type
@@ -120,15 +123,71 @@ func (rdb RethinkDB) UpdateCurrent(gun string, update MetaUpdate) error {
 	return err
 }
 
+// UpdateCurrentWithTSChecksum adds new metadata version for the given GUN with an associated
+// checksum for the timestamp it belongs to, to afford us transaction-like functionality
+func (rdb RethinkDB) UpdateCurrentWithTSChecksum(gun, tsChecksum string, update MetaUpdate) error {
+	now := time.Now()
+	checksum := sha256.Sum256(update.Data)
+	file := RDBTUFFile{
+		Timing: rethinkdb.Timing{
+			CreatedAt: now,
+			UpdatedAt: now,
+		},
+		GunRoleVersion: []interface{}{gun, update.Role, update.Version},
+		Gun:            gun,
+		Role:           update.Role,
+		Version:        update.Version,
+		Sha256:         hex.EncodeToString(checksum[:]),
+		TSchecksum:     tsChecksum,
+		Data:           update.Data,
+	}
+	_, err := gorethink.DB(rdb.dbName).Table(file.TableName()).Insert(
+		file,
+		gorethink.InsertOpts{
+			Conflict: "error", // default but explicit for clarity of intent
+		},
+	).RunWrite(rdb.sess)
+	if err != nil && gorethink.IsConflictErr(err) {
+		return &ErrOldVersion{}
+	}
+	return err
+}
+
+// Used for sorting updates alphabetically by role name, such that timestamp is always last:
+// Ordering: root, snapshot, targets, targets/* (delegations), timestamp
+type updateSorter []MetaUpdate
+
+func (u updateSorter) Len() int      { return len(u) }
+func (u updateSorter) Swap(i, j int) { u[i], u[j] = u[j], u[i] }
+func (u updateSorter) Less(i, j int) bool {
+	return u[i].Role < u[j].Role
+}
+
 // UpdateMany adds multiple new metadata for the given GUN. RethinkDB does
 // not support transactions, therefore we will attempt to insert the timestamp
-// first as this represents a published version of the repo. If this is successful,
-// we will insert the remaining roles (in any order). If any of those roles
-// errors on insert, we will do a best effort rollback, at a minimum attempting
-// to delete the timestamp so nobody pulls a broken repo.
+// last as this represents a published version of the repo.  However, we will
+// insert all other role data in alphabetical order first, and also include the
+// associated timestamp checksum so that we can easily roll back this pseudotransaction
 func (rdb RethinkDB) UpdateMany(gun string, updates []MetaUpdate) error {
+	// find the timestamp first and save its checksum
+	// then apply the updates in alphabetic role order with the timestamp last
+	// if there are any failures, we roll back in the same alphabetic order
+	var tsChecksum string
 	for _, up := range updates {
-		if err := rdb.UpdateCurrent(gun, up); err != nil {
+		if up.Role == data.CanonicalTimestampRole {
+			tsChecksumBytes := sha256.Sum256(up.Data)
+			tsChecksum = hex.EncodeToString(tsChecksumBytes[:])
+			break
+		}
+	}
+
+	// alphabetize the updates by Role name
+	sort.Stable(updateSorter(updates))
+
+	for _, up := range updates {
+		if err := rdb.UpdateCurrentWithTSChecksum(gun, tsChecksum, up); err != nil {
+			// roll back with best-effort deletion, and then error out
+			rdb.deleteByTSChecksum(tsChecksum)
 			return err
 		}
 	}
@@ -191,6 +250,18 @@ func (rdb RethinkDB) Delete(gun string) error {
 	return nil
 }
 
+// deleteByTSChecksum removes all metadata by a timestamp checksum, used for rolling back a "transaction"
+// from a call to rethinkdb's UpdateMany
+func (rdb RethinkDB) deleteByTSChecksum(tsChecksum string) error {
+	_, err := gorethink.DB(rdb.dbName).Table(RDBTUFFile{}.TableName()).GetAllByIndex(
+		"timestamp_checksum", []string{tsChecksum},
+	).Delete().RunWrite(rdb.sess)
+	if err != nil {
+		return fmt.Errorf("unable to delete timestamp checksum data: %s from database: %s", tsChecksum, err.Error())
+	}
+	return nil
+}
+
 // Bootstrap sets up the database and tables
 func (rdb RethinkDB) Bootstrap() error {
 	return rethinkdb.SetupDB(rdb.sess, rdb.dbName, []rethinkdb.Table{
diff --git a/server/storage/rethinkdb_models.go b/server/storage/rethinkdb_models.go
index 99e41d1e6d..2bb9b7761e 100644
--- a/server/storage/rethinkdb_models.go
+++ b/server/storage/rethinkdb_models.go
@@ -16,10 +16,11 @@ var (
 		Name:       RDBTUFFile{}.TableName(),
 		PrimaryKey: "gun_role_version",
 		SecondaryIndexes: map[string][]string{
-			rdbSha256Idx:        nil,
-			"gun":               nil,
-			rdbGunRoleIdx:       {"gun", "role"},
-			rdbGunRoleSha256Idx: {"gun", "role", "sha256"},
+			rdbSha256Idx:         nil,
+			"gun":                nil,
+			"timestamp_checksum": nil,
+			rdbGunRoleIdx:        {"gun", "role"},
+			rdbGunRoleSha256Idx:  {"gun", "role", "sha256"},
 		},
 		// this configuration guarantees linearizability of individual atomic operations on individual documents
 		Config: map[string]string{
diff --git a/server/timestamp/timestamp.go b/server/timestamp/timestamp.go
index ddb75ebfb4..283c7da796 100644
--- a/server/timestamp/timestamp.go
+++ b/server/timestamp/timestamp.go
@@ -50,9 +50,13 @@ func GetOrCreateTimestampKey(gun string, store storage.MetaStore, crypto signed.
 // GetOrCreateTimestamp returns the current timestamp for the gun. This may mean
 // a new timestamp is generated either because none exists, or because the current
 // one has expired. Once generated, the timestamp is saved in the store.
+// Additionally, if we had to generate a new snapshot for this timestamp,
+// it is also saved in the store
 func GetOrCreateTimestamp(gun string, store storage.MetaStore, cryptoService signed.CryptoService) (
 	*time.Time, []byte, error) {
 
+	updates := []storage.MetaUpdate{}
+
 	lastModified, timestampJSON, err := store.GetCurrent(gun, data.CanonicalTimestampRole)
 	if err != nil {
 		logrus.Error("error retrieving timestamp: ", err.Error())
@@ -65,28 +69,40 @@ func GetOrCreateTimestamp(gun string, store storage.MetaStore, cryptoService sig
 		return nil, nil, err
 	}
 
-	_, snapshot, err := snapshot.GetOrCreateSnapshot(gun, store, cryptoService)
+	snapshotTime, snapshot, err := snapshot.GetOrCreateSnapshot(gun, store, cryptoService)
 	if err != nil {
 		logrus.Debug("Previous timestamp, but no valid snapshot for GUN ", gun)
 		return nil, nil, err
 	}
+	snapshotRole := &data.SignedSnapshot{}
+	if err := json.Unmarshal(snapshot, snapshotRole); err != nil {
+		logrus.Error("Failed to unmarshal retrieved snapshot")
+		return nil, nil, err
+	}
+
+	// If the snapshot was generated, we should write it with the timestamp
+	if snapshotTime == nil {
+		updates = append(updates, storage.MetaUpdate{Role: data.CanonicalSnapshotRole, Version: snapshotRole.Signed.Version, Data: snapshot})
+	}
 
 	if !timestampExpired(prev) && !snapshotExpired(prev, snapshot) {
 		return lastModified, timestampJSON, nil
 	}
 
-	update, err := createTimestamp(gun, prev, snapshot, store, cryptoService)
+	tsUpdate, err := createTimestamp(gun, prev, snapshot, store, cryptoService)
 	if err != nil {
 		logrus.Error("Failed to create a new timestamp")
 		return nil, nil, err
 	}
+	updates = append(updates, *tsUpdate)
 
 	c := time.Now()
 
-	if err = store.UpdateCurrent(gun, *update); err != nil {
+	// Write the timestamp, and potentially snapshot
+	if err = store.UpdateMany(gun, updates); err != nil {
 		return nil, nil, err
 	}
-	return &c, update.Data, nil
+	return &c, tsUpdate.Data, nil
 }
 
 // timestampExpired compares the current time to the expiry time of the timestamp