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    Start by adding logging like this @reboot sleep 15; /root/tunnel.sh >> /tmp/some.log 2>&1 reading that log will give you a clue Commented Mar 22, 2018 at 18:17
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    does /root/tunnel.sh rely on any shell variables (or activities) performed by your login shell? Is the correct she-bang line at the top of it? Commented Mar 22, 2018 at 18:20
  • You're not mentioning what happens when the cronjob runs. Do you get an email with any error messages from the cron daemon? Commented Mar 22, 2018 at 19:00
  • @Tagwint I made it log the action and the log tell me /root/tunnel.sh: line 2: ip: command not found Does this just mean I'm not waiting it long enough or what? Since the commands work fine if I execute the script from the bash terminal or if I paste all the commands from it one by one Commented Mar 22, 2018 at 19:11
  • @JeffSchaller I didn't have the she-bang on the top of the script but I added it now and did what Tagwint told me to do to log the output of the script. since it outputs what I posted in the above comment I presume it's not a problem with variables or activities done by the shell. Commented Mar 22, 2018 at 19:15