diff --git a/pkg/cmd/roachprod/install/cockroach.go b/pkg/cmd/roachprod/install/cockroach.go
index 7a865835c489..4edd1fe7b6b2 100644
--- a/pkg/cmd/roachprod/install/cockroach.go
+++ b/pkg/cmd/roachprod/install/cockroach.go
@@ -112,17 +112,17 @@ func argExists(args []string, target string) int {
 
 // Start implements the ClusterImpl.NodeDir interface.
 func (r Cockroach) Start(c *SyncedCluster, extraArgs []string) {
-	// Check to see if node 1 was started indicating the cluster was
+	// Check to see if node 1 was started, indicating the cluster is to be
 	// bootstrapped.
-	var bootstrapped bool
+	var bootstrappable bool
 	for _, i := range c.ServerNodes() {
 		if i == 1 {
-			bootstrapped = true
+			bootstrappable = true
 			break
 		}
 	}
 
-	if c.Secure && bootstrapped {
+	if c.Secure && bootstrappable {
 		c.DistributeCerts()
 	}
 
@@ -217,7 +217,8 @@ func (r Cockroach) Start(c *SyncedCluster, extraArgs []string) {
 				args = append(args, "--locality="+locality)
 			}
 		}
-		if nodes[i] != 1 {
+		// `cockroach start` without `--join` is no longer supported as 20.1.
+		if nodes[i] != 1 || vers.AtLeast(version.MustParse("v20.1.0")) {
 			args = append(args, fmt.Sprintf("--join=%s:%d", host1, r.NodePort(c, 1)))
 		}
 		if advertisePublicIP {
@@ -271,11 +272,13 @@ func (r Cockroach) Start(c *SyncedCluster, extraArgs []string) {
 		// unhelpful empty error (since everything has been redirected away). This is
 		// unfortunately equally awkward to address.
 		cmd := "ulimit -c unlimited; mkdir -p " + logDir + "; "
+
 		// TODO(peter): The ps and lslocks stuff is intended to debug why killing
 		// of a cockroach process sometimes doesn't release file locks immediately.
 		cmd += `echo ">>> roachprod start: $(date)" >> ` + logDir + "/roachprod.log; " +
 			`ps axeww -o pid -o command >> ` + logDir + "/roachprod.log; " +
 			`[ -x /usr/bin/lslocks ] && /usr/bin/lslocks >> ` + logDir + "/roachprod.log; "
+
 		cmd += keyCmd +
 			fmt.Sprintf(" export ROACHPROD=%d%s && ", nodes[i], c.Tag) +
 			"GOTRACEBACK=crash " +
@@ -297,49 +300,96 @@ func (r Cockroach) Start(c *SyncedCluster, extraArgs []string) {
 		return nil, nil
 	})
 
-	if bootstrapped {
-		license := envutil.EnvOrDefaultString("COCKROACH_DEV_LICENSE", "")
-		if license == "" {
-			fmt.Printf("%s: COCKROACH_DEV_LICENSE unset: enterprise features will be unavailable\n",
-				c.Name)
+	if !bootstrappable {
+		return
+	}
+
+	var initOut string
+	display = fmt.Sprintf("%s: bootstrapping cluster", c.Name)
+	c.Parallel(display, 1, 0, func(i int) ([]byte, error) {
+		vers, err := getCockroachVersion(c, nodes[i])
+		if err != nil {
+			return nil, err
 		}
+		if !vers.AtLeast(version.MustParse("v20.1.0")) {
+			// `cockroach start` without `--join` is no longer supported as v20.1.
+			return nil, nil
+		}
+		sess, err := c.newSession(1)
+		if err != nil {
+			return nil, err
+		}
+		defer sess.Close()
 
-		var msg string
-		display = fmt.Sprintf("%s: initializing cluster settings", c.Name)
-		c.Parallel(display, 1, 0, func(i int) ([]byte, error) {
-			sess, err := c.newSession(1)
-			if err != nil {
-				return nil, err
-			}
-			defer sess.Close()
+		var cmd string
+		if c.IsLocal() {
+			cmd = `cd ${HOME}/local/1 ; `
+		}
 
-			var cmd string
-			if c.IsLocal() {
-				cmd = `cd ${HOME}/local/1 ; `
-			}
-			dir := c.Impl.NodeDir(c, nodes[i])
-			cmd += `
-if ! test -e ` + dir + `/settings-initialized ; then
-  COCKROACH_CONNECT_TIMEOUT=0 ` + cockroachNodeBinary(c, 1) + " sql --url " +
-				r.NodeURL(c, "localhost", r.NodePort(c, 1)) + " -e " +
-				fmt.Sprintf(`"
-SET CLUSTER SETTING server.remote_debugging.mode = 'any';
-SET CLUSTER SETTING cluster.organization = 'Cockroach Labs - Production Testing';
-SET CLUSTER SETTING enterprise.license = '%s';"`, license) + ` &&
-			touch ` + dir + `/settings-initialized
-fi
-`
-			out, err := sess.CombinedOutput(cmd)
-			if err != nil {
-				return nil, errors.Wrapf(err, "~ %s\n%s", cmd, out)
-			}
-			msg = strings.TrimSpace(string(out))
-			return nil, nil
-		})
+		binary := cockroachNodeBinary(c, 1)
+		path := fmt.Sprintf("%s/%s", c.Impl.NodeDir(c, nodes[i]), "cluster-bootstrapped")
+		url := r.NodeURL(c, "localhost", r.NodePort(c, 1))
 
-		if msg != "" {
-			fmt.Println(msg)
+		cmd += fmt.Sprintf(`
+			if ! test -e %s ; then
+				COCKROACH_CONNECT_TIMEOUT=0 %s init --url %s && touch %s
+			fi`, path, binary, url, path)
+
+		out, err := sess.CombinedOutput(cmd)
+		if err != nil {
+			return nil, errors.Wrapf(err, "~ %s\n%s", cmd, out)
+		}
+		initOut = strings.TrimSpace(string(out))
+		return nil, nil
+	})
+
+	if initOut != "" {
+		fmt.Println(initOut)
+	}
+
+	license := envutil.EnvOrDefaultString("COCKROACH_DEV_LICENSE", "")
+	if license == "" {
+		fmt.Printf("%s: COCKROACH_DEV_LICENSE unset: enterprise features will be unavailable\n",
+			c.Name)
+	}
+
+	var clusterSettingsOut string
+	display = fmt.Sprintf("%s: initializing cluster settings", c.Name)
+	c.Parallel(display, 1, 0, func(i int) ([]byte, error) {
+		sess, err := c.newSession(1)
+		if err != nil {
+			return nil, err
+		}
+		defer sess.Close()
+
+		var cmd string
+		if c.IsLocal() {
+			cmd = `cd ${HOME}/local/1 ; `
 		}
+
+		binary := cockroachNodeBinary(c, 1)
+		path := fmt.Sprintf("%s/%s", c.Impl.NodeDir(c, nodes[i]), "settings-initialized")
+		url := r.NodeURL(c, "localhost", r.NodePort(c, 1))
+
+		cmd += fmt.Sprintf(`
+			if ! test -e %s ; then
+				COCKROACH_CONNECT_TIMEOUT=0 %s sql --url %s -e "
+				    SET CLUSTER SETTING server.remote_debugging.mode = 'any';
+					SET CLUSTER SETTING cluster.organization = 'Cockroach Labs - Production Testing';
+					SET CLUSTER SETTING enterprise.license = '%s';" \
+				&& touch %s
+			fi`, path, binary, url, license, path)
+
+		out, err := sess.CombinedOutput(cmd)
+		if err != nil {
+			return nil, errors.Wrapf(err, "~ %s\n%s", cmd, out)
+		}
+		clusterSettingsOut = strings.TrimSpace(string(out))
+		return nil, nil
+	})
+
+	if clusterSettingsOut != "" {
+		fmt.Println(clusterSettingsOut)
 	}
 }
 
diff --git a/pkg/cmd/roachtest/fixtures/1/checkpoint-v20.1.tgz b/pkg/cmd/roachtest/fixtures/1/checkpoint-v20.1.tgz
index 5e50212d936a..836fbc64d4b8 100644
Binary files a/pkg/cmd/roachtest/fixtures/1/checkpoint-v20.1.tgz and b/pkg/cmd/roachtest/fixtures/1/checkpoint-v20.1.tgz differ