When I first boot up my VM I can copy text from Windows into it. However after a while the clipboard always stops working, forcing me to reboot the VM to get it working again.

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the_g_bomb’s picture

the_g_bomb CreditAttribution: the_g_bomb as a volunteer commented
Status: Active » Needs review

This is a Virtual Box issue, I believe, you could try restarting the vbox clipboard client:

$ ps -fe | grep -i clipboard

This will get you the id of any clipboards running
e.g.

drupalp+  1301     1  0 10:23 ?        00:00:00 /usr/bin/VBoxClient --clipboard

Kill it/them using

$ p=1301; kill -int $p;ps -fp $p

then restart it

$ /usr/bin/VBoxClient --clipboard

Also, though, if you have updated VirtualBox, you may want to re-install the guest additions using the virtual cd that comes with that version. I think the version in the deb repos is a little behind and the cd is usually updated when VirtualBox gets an update.
Go to Devices on your guest window and choose insert Guest Additions CD Image. That cd should now auto run.