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I used Tor at work and got informed by a security analyst that my computer was exhibiting strange behavior. She said that it was connecting to servers in Amsterdam. Though I think there were some other situation specific factors that caused her to become alarmed, is this generally a red flag if a computer in North America connects to Amsterdam? If yes, how can it be better obfuscated?

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    Before going any further, check if using Tor is allowed by your company's policies. Everywhere I have worked proxies are forbidden, and only once I was (informally) autorized to use Tor to activate a software which couldn't use corporate proxy. – Dmitry Grigoryev Aug 11 '15 at 11:33
  • @DmitryGrigoryev who or where precisely would you check, if your direct manager already said it's ok? – clipclopshop May 31 '16 at 6:38
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If you use a pluggable transport such as meek-google, meek-amazon or meek-azure, all outgoing connections will appear to go to google appengine, amazon cloudfront or microsoft azure; see https://trac.torproject.org/projects/tor/wiki/doc/meek

However, this will slow down browing speed in Tor Browser, and use bandwith on the meek backends which costs money to provide, so you should only make use of it if really necessary.

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It is not unusual for a computer to connect to "foreign" locations. So a computer in North America can connect to a computer in Amsterdam without any problems. However I guess your company runs some monitoring (or better call it surveillance) device which looks at all connections. They follow their own definitions of "unusual" and maybe a long-term connection to any non-US country is seen as unusual.

If you want to prevent this, you can edit your torrc. Open the file in a text editor and enter the lines:

EntryNodes {us}
StrictNodes 1

After you've restarted Tor it will connect to a US based server and will always use this as a first node.

If this does not work for you, you can also use bridges and pluggable transports. Go to https://bridges.torproject.org/ and get a bridge address. However some bridges are also outside the US. So you might have those problems again. Maybe the pluggable transport meek works best for you.

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