Complex things cannot be totally simplified

I consider myself a fairly experienced tech person. I used to make heavy use of tech including running my own server and writing the code necessary to conduct my research. Now, in retirement, I consider myself a tech writer. This background still does not mean all tech projects come easily to me. Such is my present situation.

Given the current state of the online world and our (my wife and myself) heavy involvement, we need to take things seriously. We finally decided to improve our security by purchasing a password manager and moving to more complex passwords. I am still in the process of trying to create a completely successful implementation.

My struggles stem from a couple of things. First, I am an impulsive problem solver. When something doesn’t work, I try something else. I often forget which of several attempts was successful making solving the same problem a second time no easier. Second, I have created for myself a very complex tech environment. Here are the factors that seem to be relevant to my present challenge:

  • Within a couple of weeks, I use 7 different devices (tablets, phone, computers)
  • These devices use multiple operating systems – MacOS, iOS, chrome
  • On these multiple devices I use four different browsers (Chrome, Firefox, Safari, Brave)
  • I have accounts on probably 30 or so online accounts. Some I use frequently and some seldom. Sometimes, I know the login and password and sometimes I do not. I often rely on stored passwords for those accounts I could not enter from memory.

The concept of a password manager is easy enough to understand. You open a service and go to the place to change the password. You create and store a more complex password in the password manager and you copy and paste this new password to the account you want to update and save. You should now be able to use this service by opening the password manager on another device you have installed the password manager on as the password managers share the new passwords you have created.

I have decided the problems I am having are due to the technology trying to be too helpful. Depending how you have set up your operating system and browsers, your passwords can be stored and autofilled. Sometimes this information is stored in multiple places on the same machine and shared across machines. So, your operating system may store this information and a browser on this device may also store the passwords. Changing the password for a site and storing this adjustment in the password manager does not necessarily change the stored passwords on your device. In some cases, I had probably 50 stored passwords associated with a browser. I could possibly delete all and turn off autofill, but my original plan was not to change every password in the password manager partly because I have relied on the stored passwords in various browsers. I hope this makes sense and explains how this process can end up being more complicated than those who promote password managers make it sound.

My present strategy has been to delete specific existing stored information on my devices for the specific sites I want to have more complex passwords. When the new passwords stored by the password manager are then saved and shared among the multiple devices. This process has to be repeated for each browser.

A password manager and complex passwords are good ideas. I certainly encourage you to make the effort. Depending on how complex your own tech world happens to be you may have an easy time making the adjustment or be in for considerable trouble shooting. If you have created something that approximates my own situation, the one suggestion I would offer is to be aware of the multiple ways old passwords may be stored on your devices.

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