.AspNet.Cookies not set in IIS virtual application when using OWIN cookie middleware with .NET Framework

I'm running a .NET framework 4.7.2 application using OWIN cookie authentication under IIS as a virtual application locally (e.g., https://example.test/cms/) but I end up in and endless redirect loop after I navigate to https://example.test/cms/ and logged in there. It validates the security token but the .AspNet.Cookies cookie does not seem to persist which causes an endless loop.

I configured the Redirect URI as https://example.test/cms/signin-oidc/ and I have a valid self-signed certificate for HTTPS. Am I missing something?

        public static void ConfigureAuthentication(IAppBuilder app)
        {
            var clientId = SsoConfig.Instance.ClientId;
            var authority = $"https://login.microsoftonline.com/{SsoConfig.Instance.TenantId}/v2.0";
            var redirectUri = SsoConfig.Instance.RedirectUri;

            var loggingCookieManager = new LoggingCookieManager();

            app.SetDefaultSignInAsAuthenticationType(CookieAuthenticationDefaults.AuthenticationType);

            app.UseCookieAuthentication(new CookieAuthenticationOptions
            {
                CookieSecure = CookieSecureOption.Always,
                ExpireTimeSpan = TimeSpan.FromHours(1),
                CookiePath = "/cms",
                CookieManager = loggingCookieManager,
            });

            app.UseOpenIdConnectAuthentication(new OpenIdConnectAuthenticationOptions
            {
                CookieManager = loggingCookieManager,
                ClientId = clientId,
                Authority = authority,
                RedirectUri = redirectUri,
                ResponseType = OpenIdConnectResponseType.CodeIdToken,
                Scope = "openid profile email offline_access",
                TokenValidationParameters = new TokenValidationParameters
                {
                    ValidateIssuer = true
                },
                RequireHttpsMetadata = true,
                SignInAsAuthenticationType = CookieAuthenticationDefaults.AuthenticationType,
            });
        }

And my Cookie Manager is just a wrapper for debugging.

    public class LoggingCookieManager : ICookieManager
    {
        private readonly ICookieManager _inner;

        public LoggingCookieManager(ICookieManager inner = null)
        {
            _inner = inner ?? new CookieManager();
        }

        public string GetRequestCookie(IOwinContext context, string key)
        {
            var val = _inner.GetRequestCookie(context, key);
            Debug.WriteLine($"GetRequestCookie: {key} = {val}");
            return val;
        }

        public void AppendResponseCookie(IOwinContext context, string key, string value, CookieOptions options)
        {
            options.SameSite = Microsoft.Owin.SameSiteMode.None; // to make sure the cookie is sent in all contexts (cross-site)
            Debug.WriteLine($"AppendResponseCookie: {key} = {value}, Path={options.Path}, SameSite={options.SameSite}, Secure={options.Secure}");
            _inner.AppendResponseCookie(context, key, value, options);
        }

        public void DeleteCookie(IOwinContext context, string key, CookieOptions options)
        {
            Debug.WriteLine($"DeleteCookie: {key}");
            _inner.DeleteCookie(context, key, options);
        }
    }

I hoped the Cookie Manager wrapper gave me some more insights but it did not. It seemed to set the cookie correctly as .AspNet.Cookies=<cookie-value-here>; path=/cms; secure; HttpOnly; SameSite=None. But the next time it called GetRequestCookie at https://example.test/cms/ the cookie was null.