diff --git a/cli/configssh.go b/cli/configssh.go
index 76b9332a69659..3741c5ceec25e 100644
--- a/cli/configssh.go
+++ b/cli/configssh.go
@@ -236,6 +236,8 @@ func (r *RootCmd) configSSH() *serpent.Command {
 			r.InitClient(client),
 		),
 		Handler: func(inv *serpent.Invocation) error {
+			ctx := inv.Context()
+
 			if sshConfigOpts.waitEnum != "auto" && skipProxyCommand {
 				// The wait option is applied to the ProxyCommand. If the user
 				// specifies skip-proxy-command, then wait cannot be applied.
@@ -244,7 +246,14 @@ func (r *RootCmd) configSSH() *serpent.Command {
 			sshConfigOpts.header = r.header
 			sshConfigOpts.headerCommand = r.headerCommand
 
-			recvWorkspaceConfigs := sshPrepareWorkspaceConfigs(inv.Context(), client)
+			// Talk to the API early to prevent the version mismatch
+			// warning from being printed in the middle of a prompt.
+			// This is needed because the asynchronous requests issued
+			// by sshPrepareWorkspaceConfigs may otherwise trigger the
+			// warning at any time.
+			_, _ = client.BuildInfo(ctx)
+
+			recvWorkspaceConfigs := sshPrepareWorkspaceConfigs(ctx, client)
 
 			out := inv.Stdout
 			if dryRun {
@@ -366,7 +375,7 @@ func (r *RootCmd) configSSH() *serpent.Command {
 				return xerrors.Errorf("fetch workspace configs failed: %w", err)
 			}
 
-			coderdConfig, err := client.SSHConfiguration(inv.Context())
+			coderdConfig, err := client.SSHConfiguration(ctx)
 			if err != nil {
 				// If the error is 404, this deployment does not support
 				// this endpoint yet. Do not error, just assume defaults.