C# skips if statement in while loop

Question

It's a twitter bot that sends tweet at sunrise/sunset. In only got it to post the first tweet. I've achieved it by using a while loop and two if statements (for each tweet). But it skips the second if statement and only executes the first one. Like it does'nt even execute what is written in the second if statement.

while (true)
{
            DateTime localTime = DateTime.Now;
            DateTime test = new DateTime(2020, 9, 11, 9, 53, 0);
            int timeComparison = DateTime.Compare(localTime, test);

            DateTime localTimeTwo = DateTime.Now;
            DateTime testTwo = new DateTime(2020, 9, 11, 9, 53, 15);
            int timeComparisonTwo = DateTime.Compare(localTimeTwo, testTwo);


                bool checkPoint = false;

                if (timeComparison > 0)
                {
                    Console.WriteLine(localTime);
                    SendTweet($"< {DateTime.Now} > Sunrise Twitter test ");
                    Console.Read();
                    checkPoint = true;
                }

                if (checkPoint == true && timeComparisonTwo > 0)
                {
                    Console.WriteLine(localTimeTwo);
                    SendTweet($"< {DateTime.Now} > Sunset Twitter test ");
                    Console.Read();
                    break;
                }
            }