diff --git a/tool/tsh/common/tsh.go b/tool/tsh/common/tsh.go
index df3554f1debb5..4fbafbee75389 100644
--- a/tool/tsh/common/tsh.go
+++ b/tool/tsh/common/tsh.go
@@ -3374,28 +3374,29 @@ func retryWithAccessRequest(
 }
 
 func promptUserForAccessRequestDetails(cf *CLIConf, req types.AccessRequest) error {
-	if cf.RequestMode != accessRequestModeRole {
-		return nil
-	}
-	// If this is a role access request, ensure that it only has one role.
-	switch len(req.GetRoles()) {
-	case 0:
-		return trace.AccessDenied("no roles to request that would grant access")
-	case 1:
-		return nil
-	default:
-		selectedRole, err := prompt.PickOne(
-			cf.Context, os.Stdout, prompt.NewContextReader(os.Stdin),
-			"Choose role to request",
-			req.GetRoles())
-		if err != nil {
-			return trace.Wrap(err)
+	if cf.RequestMode == accessRequestModeRole {
+		// If this is a role access request, ensure that it only has one role.
+		switch len(req.GetRoles()) {
+		case 0:
+			return trace.AccessDenied("no roles to request that would grant access")
+		case 1:
+			// No need to choose a role, just set request reason.
+		default:
+			selectedRole, err := prompt.PickOne(
+				cf.Context, os.Stdout, prompt.NewContextReader(os.Stdin),
+				"Choose role to request",
+				req.GetRoles())
+			if err != nil {
+				return trace.Wrap(err)
+			}
+			req.SetRoles([]string{selectedRole})
 		}
-		req.SetRoles([]string{selectedRole})
 	}
+
 	if err := setAccessRequestReason(cf, req); err != nil {
 		return trace.Wrap(err)
 	}
+
 	return nil
 }
 
diff --git a/tool/tsh/common/tsh_test.go b/tool/tsh/common/tsh_test.go
index 5cce530be144e..50bf98a7b19a8 100644
--- a/tool/tsh/common/tsh_test.go
+++ b/tool/tsh/common/tsh_test.go
@@ -48,6 +48,7 @@ import (
 	"github.com/ghodss/yaml"
 	"github.com/google/go-cmp/cmp"
 	"github.com/google/go-cmp/cmp/cmpopts"
+	"github.com/google/uuid"
 	"github.com/gravitational/trace"
 	"github.com/stretchr/testify/assert"
 	"github.com/stretchr/testify/require"
@@ -1975,6 +1976,20 @@ func TestSSHAccessRequest(t *testing.T) {
 			_, err = rootAuth.GetAuthServer().UpsertUser(ctx, alice)
 			require.NoError(t, err)
 
+			err = Run(ctx, []string{
+				"logout",
+			}, setHomePath(tmpHomePath))
+			require.NoError(t, err)
+
+			err = Run(ctx, []string{
+				"login",
+				"--insecure",
+				"--proxy", proxyAddr.String(),
+				"--user", "alice",
+			}, setHomePath(tmpHomePath), setMockSSOLogin(rootAuth.GetAuthServer(), alice, connector.GetName()))
+			require.NoError(t, err)
+
+			requestReason := uuid.New().String()
 			// the first ssh request can fail if the proxy node watcher doesn't know
 			// about the nodes yet, retry a few times until it works
 			require.Eventually(t, func() bool {
@@ -1984,7 +1999,7 @@ func TestSSHAccessRequest(t *testing.T) {
 					"--debug",
 					"--insecure",
 					"--request-mode", tc.requestMode,
-					"--request-reason", "reason here to bypass prompt",
+					"--request-reason", requestReason,
 					fmt.Sprintf("%s@%s", user.Username, sshHostname),
 					"echo", "test",
 				}, setHomePath(tmpHomePath))
@@ -1994,6 +2009,12 @@ func TestSSHAccessRequest(t *testing.T) {
 				return err == nil
 			}, 10*time.Second, 100*time.Millisecond, "failed to ssh with retries")
 
+			requests, err := rootAuth.GetAuthServer().GetAccessRequests(ctx, types.AccessRequestFilter{})
+			require.NoError(t, err)
+			require.True(t, slices.ContainsFunc(requests, func(request types.AccessRequest) bool {
+				return request.GetRequestReason() == requestReason
+			}), "access request with the specified reason was not found")
+
 			// now that we have an approved access request, it should work without
 			// prompting for a request reason
 			err = Run(ctx, []string{