You can also watch this video (and subscribe) on YouTube or PeerTube.
This is basically the video form of this reply on the Privacy Guides forum, and the new Tor Overview page published recently to Privacy Guides, so if you prefer text you just can read those things I’ve written and you’ll be all caught up :)
Safely Connecting to Tor
Before connecting to Tor, you should carefully consider what you're looking to accomplish by using Tor in the first place, and who you're trying to hide your network activity from.
If you live in a free country, are accessing mundane content via Tor, aren't worried about your ISP or local network administrators having the knowledge that you're using Tor, and want to help de-stigmatize Tor usage, you can likely connect to Tor directly via standard means like Tor Browser without worry.
If you have the ability to access a trusted VPN provider and any of the following are true, you almost certainly should connect to Tor through a VPN:
You already use a trusted VPN provider
Your threat model includes an adversary which is capable of extracting information from your ISP
Your threat model includes your ISP itself as an adversary
Your threat model includes local network administrators before your ISP as an adversary
Because I already generally recommend that the vast majority of people use a trusted VPN provider for a variety of reasons, the following recommendation about connecting to Tor via a VPN likely applies to you. There is no need to disable your VPN before connecting to Tor, as some online resources would lead you to believe.
Connecting directly to Tor will make your connection stand out to any local network administrators or your ISP. Detecting and correlating this traffic has been done in the past by network administrators to identify and deanonymize specific Tor users on their network. On the other hand, connecting to a VPN is almost always less suspicious, because commercial VPN providers are used by everyday consumers for a variety of mundane tasks like bypassing geo-restrictions, even in countries with heavy internet restrictions.
Therefore, you should make an effort to hide your IP address before connecting to the Tor network. You can do this by simply connecting to a VPN (through a client installed on your computer) and then accessing Tor as normal, through Tor Browser for example. This creates a connection chain like:
You → VPN → Tor → Internet
From your ISP's perspective, it looks like you're accessing a VPN normally (with the associated cover that provides you). From your VPN's perspective, they can see that you are connecting to the Tor network, but nothing about what websites you're accessing. From Tor's perspective, you're connecting normally, but in the unlikely event of some sort of Tor network compromise, only your VPN's IP would be exposed, and your VPN would additionally have to be compromised to deanonymize you.
This is not censorship circumvention advice, because if Tor is blocked entirely by your ISP, your VPN likely is as well. Rather, this recommendation aims to make your traffic blend in better with commonplace VPN user traffic, and provide you with some level of plausible deniability by obscuring the fact that you're connecting to Tor from your ISP.
I very strongly discourage combining Tor with a VPN in any other manner. Do not configure your connection in a way which resembles any of the following:
You → Tor → VPN → Internet
You → VPN → Tor → VPN → Internet
Any other configuration
Some VPN providers and other publications will occasionally recommend these bad configurations to evade Tor bans (exit nodes being blocked by websites) in some places. Normally, Tor frequently changes your circuit path through the network. When you choose a permanent destination VPN (connecting to a VPN server after Tor), you're eliminating this advantage and drastically harming your anonymity.
Setting up bad configurations like these is difficult to do accidentally, because it usually involves either setting up custom proxy settings inside Tor Browser, or setting up custom proxy settings inside your VPN client which routes your VPN traffic through the Tor Browser. As long as you avoid these non-default configurations, you're probably fine.
A note on VPN/SSH Fingerprinting: The Tor Project notes that theoretically using a VPN to hide Tor activities from your ISP may not be foolproof. VPNs have been found to be vulnerable to website traffic fingerprinting, where an adversary can still guess what website is being visited, because all websites have specific traffic patterns.
Therefore, it's not unreasonable to believe that encrypted Tor traffic hidden by a VPN could also be detected via similar methods. There are no research papers on this subject, and we still consider the benefits of using a VPN to far outweigh these risks, but it is something to keep in mind.
If you still believe that pluggable transports (bridges) provide additional protection against website traffic fingerprinting that a VPN does not, you always have the option to use a bridge and a VPN in conjunction.
Determining whether you should first use a VPN to connect to the Tor network will require some common sense and knowledge of your own government's and ISP's policies relating to what you're connecting to. However, again in most cases you will be better off being seen as connecting to a commercial VPN network than directly to the Tor network. If VPN providers are censored in your area, then you can also consider using Tor pluggable transports (e.g. Snowflake or meek bridges) as an alternative, but using these bridges may arouse more suspicion than standard WireGuard/OpenVPN tunnels.
What Tor is Not
The Tor network is not the perfect privacy protection tool in all cases, and has a number of drawbacks which should be carefully considered. These things should not discourage you from using Tor if it is appropriate for your needs, but they are still things to think about when deciding which solution is most appropriate for you.
Tor is not a free VPN
The release of the Orbot mobile app has lead many people to describe Tor as a "free VPN" for all of your device traffic. However, treating Tor like this poses some dangers compared to a typical VPN.
Unlike Tor exit nodes, VPN providers are usually not actively malicious. Because Tor exit nodes can be created by anybody, they are hotspots for network logging and modification. In 2020, many Tor exit nodes were documented to be downgrading HTTPS traffic to HTTP in order to hijack cryptocurrency transactions. Other exit node attacks such as replacing downloads via unencrypted channels with malware have also been observed. HTTPS does mitigate these threats to an extent.
As we've alluded to already, Tor is also easily identifiable on the network. Unlike an actual VPN provider, using Tor will make you stick out as a person likely attempting to evade authorities. In a perfect world, Tor would be seen by network administrators and authorities as a tool with many uses (like how VPNs are viewed), but in reality the perception of Tor is still far less legitimate than the perception of commercial VPNs, so using a real VPN provides you with plausible deniability, e.g. "I was just using it to watch Netflix," etc.
Tor usage is not undetectable
Even if you use bridges and pluggable transports, the Tor Project provides no tools to hide the fact that you are using Tor from your ISP. Even using obfuscated "pluggable transports" or non-public bridges do not hide the fact that you are using a private communications channel. The most popular pluggable transports like obfs4 (which obfuscates your traffic to "look like nothing") and meek (which uses domain fronting to camouflage your traffic) can be detected with fairly standard traffic analysis techniques. Snowflake has similar issues, and can be easily detected before a Tor connection is even established.
Pluggable transports other than these three do exist, but typically rely on security through obscurity to evade detection. They aren't impossible to detect, they are just used by so few people that it's not worth the effort building detectors for them. They shouldn't be relied upon if you specifically are being monitored.
It is critical to understand the difference between bypassing censorship and evading detection. It is easier to accomplish the former because of the many real-world limitations on what network censors can realistically do en masse, but these techniques do not hide the fact that you—specifically you—are using Tor from an interested party monitoring your network.
Tor Browser is not the most secure browser
Anonymity can often be at odds with security: Tor's anonymity requires every user to be identical, which creates a monoculture (the same bugs are present across all Tor Browser users). As a cybersecurity rule of thumb, monocultures are generally regarded as bad: Security through diversity (which Tor lacks) provides natural segmentation by limiting vulnerabilities to smaller groups, and is therefore usually desirable, but this diversity is also less good for anonymity.
Additionally, Tor Browser is based on Firefox's Extended Support Release builds, which only receives patches for vulnerabilities considered Critical and High (not Medium and Low). This means that attackers could (for example):
Look for new Critical/High vulnerabilities in Firefox nightly or beta builds, then check if they are exploitable in Tor Browser (this vulnerability period can last weeks).
Chain multiple Medium/Low vulnerabilities together until they get the level of access they're looking for (this vulnerability period can last months or longer).
Those at risk of browser vulnerabilities should consider additional protections to defend against Tor Browser exploits, such as using Whonix in Qubes to contain your Tor browsing in a secure VM and protect against leaks.
Why You Should Connect to Tor with a VPN