I will share a couple of examples of existing software-aided contemplative practices, take a bow to a related mind control controversy, and mention my own software-aided contemplative initiative.
First, I will ignore the plethora of Mindfulness apps and related software. Contemplating one’s own inner sensations during relative relaxation is useful, it’s not the same as making room for organized thinking, or even reorganizing on purpose.
I prefer to define contemplation in keeping with its more common usage, that is, something like “reflecting on what you are thinking about.” Pondering. Contemplate literally means to create a temple for a matter of interest or concern. When that originates with the mind, it’s a form of mental contemplation.
HeartMath is the first example that comes to mind. It originated as practices involving mental contemplation and aims to help the body recognize outside stressors as positive vibes in the body. The practices let you notice how the body, particularly the heart, responds to contemplating stressors. [1-footnote below]
Another category is software-hardware interfaces, such as those for Eye Movement Desensitization and Reprocessing Therapy, where a person contemplates traumatic events or limiting beliefs and a counselor provides feedback and direction based on what is detected by the interface.
Revisiting-the-past kinds of feedback have a dubious side. Those who have benefited are free to take offense, though none is intended. The reality is, contemplative interfaces that require an approved objective and confidential assistant evoke for me of the dangerous power of scientology with its e-meters and declarations of ‘clear.’ 
When contemplative methods link the judgment of others to the confessional spirit that underlies contemplation, it puts us at risk of caring more about what others think than what we do. “Forgive me father, for I have sinned.” It is possible in this way for contemplation to be reduced to people-pleasing.
Taken further, when confession to another (or inability to hide, as in Big Brother) is tied to positive (or negative) judgment in a way that is all encompassing and systematic, the desire for (or fear of) mind control arises.
From a more balanced perspective, there’s still the issue of the potentially embarrassing prospect of no place to hide, and thus people might experience aversion to systematic contemplation.
Back to the question at hand. In 2018, I development on a systematic contemplation tool based on the ONT - Novel View algorithm. I created a White Paper version of the project should you wish to know more about the vision.
Currently it's an alpha application built as a WordPress plugin and called Journey. At present it requires something larger than a mobile phone.
Original publish date Nov 3, 2017 (updated)
 At first, HeartMath technology was limited to certified health professionals. That’s changed and in the last five years or so there are personal monitors and apps and whatnot. It’s debatable how necessary those are (I benefited without them), but they exist. I also very much appreciate HeartMath’s focus on outreach to high risk populations such as vets, emergency responders, and disaster survivors. I’m not fond of their “global initiative,” consciousness-raising arm however.
 I generally sympathize with those who have been brainwashed by scientology. Good initiative, bad judgment. Going Clear: Scientology and the Prison of Belief - Official Trailer
What are examples of or more general prospects for software-aided contemplative practice? (original Quora question)