PfSense Upgrade system or Packages first
I want to upgrade from 2.1 to 2.1.3 but I have a few packages I have not updated in a while. Should I update those packages and then update pfsense or update pfsense and then the packages.
Does it matter?
I updated the packages first, then the upgrade and noticed that pfSense automatically reinstalled the packages after it rebooted. That said, I'd still recommend reading the guide(s), https://doc.pfsense.org/index.php/Upgrade_Guide as there are different recommendations for bare metal vs. virtual and even regular vs. embedded.
If pfSense is your Internet gateway, I think the crucial step is to download local copies (or find your original install media) just in case you need to reinstall after losing Internet access.
Here's what worked for me on my bare metal non-embedded firewall:
1. Backup up config. (Menu; "Diagnostics"; "Backup/Restore"; Backup area: "All"; "Download Configuration")
2. Downloaded the 2.1.3 image to my workstation so that I could do a complete reinstall easily.
3. Updated all the packages. (Menu; "System"; "Packages"; "Installed Packages")
4. Upgraded pfSense. (Menu; "System"; "Firmware"; "Auto Update".
Worked flawlessly and I never needed the backup plan.
As far as I know the packages will be reinstalled after the upgrade anyway so you gain nothing by trying to reinstall them before the upgrade.
After update pfSense always installs the latest versions of the packages, not the same versions that were installed before update, right?