People have mentioned in IRC, in the WMCS annual survey, and on Talk pages that https://wikitech.wikimedia.org/wiki/Help:Access_to_Toolforge_instances_with_PuTTY_and_WinSCP needs an update.
I suggest the following improvements (there may be more, this is just after an initial review without any subject expertise in this area):
[ ] Add an introductory line or two about *why* someone may need or want to read this doc. For example, "To upload multiple files and manage folder structure for your Toolforge account or your tools, you can use an ssh-compatible file or FTP browser instead of the command line."
[ ] Improve doc structure: Choosing and installing a file or FTP browser to use seems like the first step, but Filezilla is added as an afterthought at the bottom of the page. Perhaps it should be moved up to an earlier section.
[ ] Clarify / link to info about Toolforge bastion servers upon first mentioning them, and standardize the language ("bastion host" vs "bastion server"). https://wikitech.wikimedia.org/wiki/Portal:Toolforge/About_Toolforge#Bastion_hosts. See comment on Talk page as well: https://wikitech.wikimedia.org/wiki/Help_talk:Access_to_Toolforge_instances_with_PuTTY_and_WinSCP#Bastion_hosts
[ ] Rewrite the sentence "You are likely going to set up connections to each of the login servers". Instead, tell the reader which server they must set up connections to and why, or tell them to do both. Remove the ambiguity.
[ ] Clarify: how does one "Make sure private key is compatible with putty"? How would I know if it wasn't?
[ ] Check validity of all screenshots and update them for a reasonably recent version of the software.
[ ] Improve the page structure and readability: create subsections for each of the steps under "How to set up...". If you think there's not enough content for page sections, there should at least be a numbered list of steps within each section. In the "How to set up WinSCP" section, crucial instructions are in image captions. The should be placed in normal paragraph text and/or represented as a list of steps.
[ ] Review comments on Talk page and add to or update the doc to try to resolve the issues they mention.
[ ] Go through the process described yourself, and verify that the information on the page enables you to complete the task of setting up each of the mentioned file transfer tools to connect to a Toolforge account and transfer/create files with the necessary and correct permissions settings.
[ ] There seems to be some ambiguity around file permissions and ownership, as indicated by both the Troubleshooting section. If it's a common issue that the file system permissions on the tool directory are easy to mess up, maybe it would also be good to add some additional troubleshooting instructions like what [[ https://wikitech.wikimedia.org/wiki/User:Dvorapa/Toolforge_for_beginners/Daily_basic_tasks | User:Dvorapa has put on their userpage ]] about how to unify ownership even if you changed files under the wrong user or forgot to "become" your tool. (i.e. if owner of files you changed using your browser is username and the owner of files you changed using your command line is my_tool.)
With these suggestions, I'm opening this task up for anyone to work on. If you claim this task and have questions, you can get help on one of the Cloud Services communications channels listed here: https://wikitech.wikimedia.org/wiki/Help:Access_to_Toolforge_instances_with_PuTTY_and_WinSCP#Communication_and_support