I'll try my best, but obviously these are just my thoughts and a lot of other people don't necessarily agree with me.
I think all authoritarian governments rely on a chunk of their population to stay in power. This population can be very small, but sufficient.
In order to maintain their popularity they rely on:
1. Lack of education
2. Strong propaganda
3. Poverty
4. Social welfare
5. Religion & ideology
6. Fear of enemy
Within their target demographics.
So, they will end up with chunks of population who are uneducated, poor, strongly reliant on government welfare that are actually thankful for the government for their social welfare and cultural/religious alignment.
The pro-democracy people are usually middle class citizens. How do you fight uneducated, religiously/culturally motivated people with tame middle class citizens? It's not doable. That's why Taliban takes control of Afghanistan.
The only thing that I've seen work is this:
1. You try to keep communications alive with population. Google leaving a country? There couldn't be anything worse.
2. You incentivize government/regimes to stay as open as possible.
3. You wait decades for paradigm shifts within populations.
As for #1, let me give you an example. ~25 years ago I was 7. I lived in Iran. There was no internet. TV & Radio are government controlled and the country was too poor for people to travel abroad.
The _only_ thing that kept us connected to the outside world was... soccer.
Iranian state TV would broadcast a few soccer games a week (not live). For a massive chunk of the population, the only way to see there are _other_ type of people, not name Ali, Hussain, Muhammed, etc, and instead named Alessandro, Paolo, David, whatever, was soccer. Something simple like this can really keep the mind open. Allows you to realize there are other ways.
Fast forward a few years, a "reform" government was in place. The regime was relatively incentivized to talk to the US. Thus, they allowed Internet. The reform government allowed music and film to flourish again. As a result of economic growth a lot of Iranians were traveling abroad (from Turkey and Dubai to all over Europe) and as a result the middle class got more and more "western".
Fast forward to Donald Trump leaving the JCPOA, putting a "maximum pressure" campaign against Iran.
The economy went to shit (it's really a humanitarian crisis now). The government, scared of riots, locked everything down. All European brands/companies have left the country and the government is pushing to close down internet altogether.
A decade ago Iranians were pushing for democracy (Green Movement). Now, their only concern is survival. There is no hope anymore. The population is getting poorer and poorer, less and less educated.
So my question after this story is, do you think Google leaving Russia will end up helping Russians get more educated, more wealthy, more connected to the free world?
Or would it push them to the direction of poverty, isolation and disconnect?
Iran 10 years ago (before maximum pressure campaign by the republicans) was on the path to be something like Turkey. Not totally free, but somewhat OK ish country. Now it's on the path to be another North Korea (if this direction continues for another 15-20 years)
Sorry this wasn't a well written, well thought piece. It was an anecdotal dump of thoughts, but hopefully I managed to make a point.