1 step forward...

I think the ever-present trap is thinking you've learned how to do it, or at least that you understand all of the factors in play. With success and experience, inevitably comes confidence... which, in a screwed up way, can work against you. I think there's a certain mindset at the root of it, that creates the right circumstances... so rather than trying to control the circumstances directly, find that thing which lives upstream from that layer. That this isn't a result of satisfying the right circumstances, but experiencing yourself sexually. Analysis itself is the enemy.

You are actually rewiring your mind-body connection each time you practice relaxing your body, clearing your mind, focusing on your pelvic region, and practicing Kegel exercises and different positions. Your mind and whole body needs to be rested also for each session. There will be down times that we all experience and it seems as nothing is happening. Be assured, you are always moving forward. You did state that a few weeks ago you began making progress. That's a great sign of things to come. Be patient, stick to the plan, and you will be surprised how your mind and body respond.

Your diligence will be rewarded.

I felt like a month ago I began making some progress... throwing out expectations, quieting my mind, experimenting with different positions and contractions...

Those are all good practices which you should continue doing.

I know that I should be relaxing and keep my mind quiet but is this natural?

I think it is natural in the sense it is a learned behavior which promotes healthy life choices, when your mind is quiet, your own inner wisdom can whisper its knowledge to your ego consciousness.

What should I do? Any advice for a newbie?

You could read and try some of the advice given in these related posts -> Dealing with frustration, Just bought my first aneros, but need help., Just got aneros & Help For New Male User. You will soon see a familiar theme being expressed, namely you need to have patience.
Perhaps you'll recall in the introductory PM I sent you when you first joined the forum I said :

The path/journey toward the Super-O is more than the attaining of a certain state of sensual/sexual/physical arousal. This process involves your "awakening" your prostate, listening to your body, becoming more attuned to the many subtle feelings being generated and then gently nurturing those feelings into heightened physical and emotional states. Each person is unique so the steps along the pathway will differ for each one of us, there is no ONE formula for progress.
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The time frame for this process of "rewiring" can vary widely from individual to individual, some users have gotten to a Super-O almost immediately, others have taken more than a year or even two to reach that goal. Nearly a quarter of the men using the Aneros took longer than a year to get there

Progress in one's Aneros 'rewiring' journey is rarely consistently linear, there may be 'lag times', plateaus or side detours, but these are all part of the learning process too. Perspicacity, Perseverance and Patience are needed here, what you are already doing is probably fine but don't be reluctant to try alternate techniques. Stubbornly staying with a technique which is not pleasurable is counterproductive, be adventuresome and remain hopeful with a positive attitude, it is the continued practice itself which pushes the progress, sometimes in undetectable increments, sometimes in big steps.
Good Vibes to You !

Reading these forums while listening to music somehow makes it feel epic. Haha. I've felt like that many time @thunderfox07 but here recently I've come to 'try' and accept that my session 'succes'- very subjective, is much like a rollar coaster ride. As soon as I'm certain I had it forever it's gone. Just vanished. But thats not the case, every two steps back you take you'll take 3 more forward, so long as you stick to it and have a submissive mindset. Analysis is the enemy, and when I first began I thought that analysis was essential to learning the steps to an orgasm, but there are no steps. 🙂 @Clenchy has given very sound advice.

2 steps back?
I felt like a month ago I began making some progress... throwing out expectations, quieting my mind, experimenting with different positions and contractions...

But now I feel like I'm at a standstill... I know that I should be relaxing and keep my mind quiet but is this natural? What should I do? Any advice for a newbie?

Every time I figure out something new or make some sort of progress I let it get into my head and I end up having issues.

I think its important to go into every session with the idea that 'anything can happen' and not 'im going to have orgasm X because last time I had orgasm X and it felt good'.

Relaxing, when people are speaking in context of the aneros, isnt about trying to relax in a traditional sense of the word as youll likely just fall asleep, rather relaxing with the aneros is about specifically letting go of expectations and letting go of apprehensions and not much else.

Being in the mood for 'sexytime' helps a lot. Forcing it will get you no place fast. If you find that you are currently forcing it and want to stop doing so: don't let a lesser frequency of sessions make the fewer sessions seem more significant, or important, because that is a pitfall that will cause the most problems.