When downloading a windows steam game over Ubuntu Wine, I get the error "content server unreachable"

I recently botched a dual-boot install job of windows and ubuntu, and just went full Ubuntu.

I'm trying to get my steam games to run via wine. I downloaded the latest version of Wine, and then I downloaded the latest version of the windows steam installer and ran

sudo wine SteamSetup.exe

It successfully installed steam and I can get inside, but it seems that all network features are unavilable. I can see that my friends are online, but I can't access the store. When I download my games, I get the error

An error occurred while installing [Game Name] (content servers are unreachable)

None of the tutorials I've followed have mentioned anything about this issue, and it happens whether I install Steam through the terminal, with winetricks, or with PlayOnLinux.

What's going on, here?

EDIT:

Here's the Steam developer console:

Failed to init SteamVR because it isn't installed
Couldn't create IPolicyConfigVista: 0x80040154
ExecCommandLine: ""C:\Program Files (x86)\Steam\Steam.exe" -no-cef-sandbox -lognetapi -console"
IPC server is in my process - could/should be using an in process pipe
System startup time: 14.31 seconds
Crypto API failed certificate check, error flags 0x00000008 for '/C=US/ST=Massachusetts/L=Cambridge/O=Akamai Technologies, Inc./CN=a248.e.akamai.net'
Crypto API failed certificate check, error flags 0x00000008 for '/C=US/ST=Massachusetts/L=Cambridge/O=Akamai Technologies, Inc./CN=a248.e.akamai.net'
Crypto API failed certificate check, error flags 0x00000008 for '/C=US/ST=Massachusetts/L=Cambridge/O=Akamai Technologies, Inc./CN=a248.e.akamai.net'
Crypto API failed certificate check, error flags 0x00000008 for '/C=US/ST=Massachusetts/L=Cambridge/O=Akamai Technologies, Inc./CN=a248.e.akamai.net'
Crypto API failed certificate check, error flags 0x00000008 for '/C=US/ST=Massachusetts/L=Cambridge/O=Akamai Technologies, 
Inc./CN=a248.e.akamai.net'
CAPIJobRequestUserStats - Server response failed 2
"
Crypto API failed certificate check, error flags 0x00000008 for 
'/C=US/ST=Massachusetts/L=Cambridge/O=Akamai Technologies, 
Inc./CN=a248.e.akamai.net'
GameAction [AppID 8170, ActionID 1] : LaunchApp failed with AppError_18 with ""
GameAction [AppID 8170, ActionID 1] : LaunchApp changed task to Failed with ""
GameAction [AppID 8170, ActionID 2] : InstallApps waiting for user 
response to ShowEula "http://store.steampowered.com/eula/8170_eula_1"
GameAction [AppID 8170, ActionID 2] : InstallApps continues with user 
response "ShowEula"
GameAction [AppID 8170, ActionID 2] : InstallApps changed task to 
CreateNextApp with ""
saving roaming config store to 'sharedconfig.vdf'
roaming config store 2 saved successfully
GameAction [AppID 8170, ActionID 2] : InstallApps failed with 
AppError_21 with ""

Solution 1:

I received a solution to my problem in the first post of this thread that I made on the wine forums:

https://forum.winehq.org/viewtopic.php?f=8&t=30767

Go to the link that they provide and edit the config file as specified.

For the store not working the flag is -no-cef-sandbox

For the content server error, a bug was filed here

For now there's a workaround given that requires editing a file in the Steam/config directory. Comment #4 has the workaround: https://bugs.winehq.org/show_bug.cgi?id=45329#c4

I found out the difference between my two Steam installations - the one that works has a different config in drive_c/Program Files/Steam/config/config.vdf

After installing Steam in a fresh WINEPREFIX, downloading games won't work. Open the mentioned config, and under:

"InstallConfigStore"  
{  
  "Software"  
  {  
    "Valve"  
    {  
      "Steam"  
       {

add the following entry (for me it's directly under "cip" and "CM"):

"CS" "valve511.steamcontent.com;valve501.steamcontent.com;valve517.steamcontent.com;valve557.steamcontent.com;valve513.steamcontent.com;valve535.steamcontent.com;valve546.steamcontent.com;valve538.steamcontent.com;valve536.steamcontent.com;valve530.steamcontent.com;valve559.steamcontent.com;valve545.steamcontent.com;valve518.steamcontent.com;valve548.steamcontent.com;valve555.steamcontent.com;valve556.steamcontent.com;valve506.steamcontent.com;valve544.steamcontent.com;valve525.steamcontent.com;valve567.steamcontent.com;valve521.steamcontent.com;valve510.steamcontent.com;valve542.steamcontent.com;valve519.steamcontent.com;valve526.steamcontent.com;valve504.steamcontent.com;valve500.steamcontent.com;valve554.steamcontent.com;valve562.steamcontent.com;valve524.steamcontent.com;valve502.steamcontent.com;valve505.steamcontent.com;valve547.steamcontent.com;valve560.steamcontent.com;valve503.steamcontent.com;valve507.steamcontent.com;valve553.steamcontent.com;valve520.steamcontent.com;valve550.steamcontent.com;valve531.steamcontent.com;valve558.steamcontent.com;valve552.steamcontent.com;valve563.steamcontent.com;valve540.steamcontent.com;valve541.steamcontent.com;valve537.steamcontent.com;valve528.steamcontent.com;valve523.steamcontent.com;valve512.steamcontent.com;valve532.steamcontent.com;valve561.steamcontent.com;valve549.steamcontent.com;valve522.steamcontent.com;valve514.steamcontent.com;valve551.steamcontent.com;valve564.steamcontent.com;valve543.steamcontent.com;valve565.steamcontent.com;valve529.steamcontent.com;valve539.steamcontent.com;valve566.steamcontent.com;valve165.steamcontent.com;valve959.steamcontent.com;valve164.steamcontent.com;valve1611.steamcontent.com;valve1601.steamcontent.com;valve1617.steamcontent.com;valve1603.steamcontent.com;valve1602.steamcontent.com;valve1610.steamcontent.com;valve1615.steamcontent.com;valve909.steamcontent.com;valve900.steamcontent.com;valve905.steamcontent.com;valve954.steamcontent.com;valve955.steamcontent.com;valve1612.steamcontent.com;valve1607.steamcontent.com;valve1608.steamcontent.com;valve1618.steamcontent.com;valve1619.steamcontent.com;valve1606.steamcontent.com;valve1605.steamcontent.com;valve1609.steamcontent.com;valve907.steamcontent.com;valve901.steamcontent.com;valve902.steamcontent.com;valve1604.steamcontent.com;valve908.steamcontent.com;valve950.steamcontent.com;valve957.steamcontent.com;valve903.steamcontent.com;valve1614.steamcontent.com;valve904.steamcontent.com;valve952.steamcontent.com;valve1616.steamcontent.com;valve1613.steamcontent.com;valve958.steamcontent.com;valve956.steamcontent.com;valve906.steamcontent.com"

I don't know if the whitespace matters, here it's four tab characters (0x09) "CS" two tabs and the rest, on one line. Without the ">".