The psychology of WordPress upgrades & plugins

WordCamp Portland was last month. Although WordPress 2.8 has made upgrading one-click easy, there was a lot of shared sentiment about upgrades and plugins. These beliefs boil down into two groups and are summarized with the following statements:

  • “I don’t run WordPress with any plugins whatsoever because an upgrade to the core of WordPress could break a plugin and mess up my site.”
  • “I don’t upgrade WordPress because I am not sure which plugins will break.” This includes the unspoken corollary that the site is left vulnerable to attack if any given upgrade is security-related.

I do not know what other folks are using plugins for, but on my site, they are grouped into “must-haves” and “fluff.” If any of the must-have plugins break, the upgrade is a deal-breaker. I won’t do it. If any of the fluff breaks, I could probably deal with it. I would not be happy, and would anxiously be awaiting an upgrade to the broken plugin (or researching alternatives that do work), but the site would not be down. The trick is to run very few must-have plugins and make sure they are from reliable sources that seem to have enough development resources to test against betas and upgrades. That last bit is a tough call for a newbie — how do you gauge a source’s reliability? — but it becomes easier with time and experience.

To demonstrate this, let me share with you my must-haves as well as the collection of everything else. You will see that there are really only two plugins that, if broken, would badly mess up my site. Those plugins come from, what seems like to me, trustworthy, reliable, hard-working sources — sources that would not be a let-down during big upgrades.

My Must-Haves

These are the must-have plugins I am running on my site. Your list may vary.

  • Akismet – This is the canonical spam blocker.
  • OpenID – This allows me to log into other sites using my Netninja login.

Basically, my site (and my access to other sites) would not be functioning optimally without either of these two plugins. I am not worried about Akismet breaking in an upgrade because the publisher is WordPress. I am also not worried about the OpenID plugin breaking during an upgrade because it seems to have an active developer community behind it. There are frequent bugfixes and feature enhancements, such that I feel they are keeping on top of the WordPress 2.9 beta testing.

My Must-Haves With Workarounds

These would have gone in the must-have group, but they automate tasks that I am confident enough in my skills to manually perform, if needed. Of course, I would prefer the automated way.

  • Bad Behavior – Another spam blocker. This one is less WordPress-specific and is just a WordPress-plugin-wrapper around a more generic spam-bot catcher. If I had to, I could just fall back to using only Akismet.
  • Maintenance Mode – This plugin shows a nice little message stating that the site is down for maintenance. Previous to this, I would manually tweak the .htaccess file to enable HTTP-auth password security, with the message “down for maintenance,” but this plugin is more clean.
  • Twitter Tools – New posts get tweeted. I could always do this manually or not at all.
  • WP Super Cache – I do not expect to get Slashdotted or Dugg-effected any time soon, but if I did, I can always fall back to the good ol’ .htaccess redirect to a static file routine. A bit of a pain, yes, but do-able. If you run a higher-traffic site than I, you would probably want this in the above section.


Everything in this section is icing on the cake. It is UI fluff that makes me happy, but does not functionally effect the site.

  • After The Deadline – This plugin checks spelling and grammar. Firefox itself has an integrated spellchecker, and I often find my grammar is okay.
  • Breadcrumb – This provides a navigational set of breadcrumbs across the top of “pages” (as opposed to “posts”), showing the category hierarchy back to the top.
  • Clean Archives Reloaded – This is a fancy way to get to the archives, but I find people typically arrive at archived pages via search.
  • Extra Sentence Space – I am often anal about print, including text published on the internet. Something that has always bugged me about HTML is that multiple spaces get coalesced into a single space. A sentence ends in two spaces! Period! Space-space! This plugin prevents that double-space-coalescing, taking the two spaces I type into the WordPress editor and making them two spaces when you read the post.
  • FeedBurner FeedSmith – This plugin provides statistics for the RSS feed. It’s nerdy and nice to have. I should probably review the stats more than I do.
  • Get Comments Count – This plugin displays a dynamic image containing text like “3 comments” in the RSS feed. The RSS content itself stays the same, but the linked image updates to display the number of comments. This is mainly a nicety for when the feed gets syndicated to LiveJournal.
  • Google Analytics for WordPress – This integrates the blog to my Google Analytics account. That’s another thing I should probably be checking more often.
  • Google XML Sitemaps – This provides Google with a nice little concise description of the website, so it does not have to crawl the entire site as often.
  • RSS Footer – To dissuade content from being stolen by spammers and posted on a fake linkblog, this plugin provides attribution and a link back at the end of each RSS article.
  • StatPress Reloaded – You would think I had enough stats already. This is a statistics plugin I actually (sometimes) use, providing integrated stats and realtime viewing of traffic. It is not as comprehensive as Google or Feedburner, but this one I actually remember to check occasionally.
  • Subscribe To Comments – This allows commenters to receive email followups.
  • Wordbook – Most of my LiveJournal and MySpace friends have moved on to Facebook. This updates Facebook with a little blurb each time I post something new. I may actually drop this soon. At one point in the past Wordbook would include an excerpt and thumbnail (if your post contained a picture), but it is strictly the post’s title now. Twitter-Tools informs Twitter using just the title and a link to the blog post, and my Twitter posts get pushed to Facebook, so Wordbook in its current form provides very little anymore.
  • WPtouch iPhone Theme – This is a dynamic theme for the iPhone. If someone connects with their iPhone, this theme automatically kicks in and makes the user experience optimized for that screen and input method.
  • Yet Another Related Posts Plugin – Do you see those “related by keyword” links below? This plugin automatically generates those.


I really have very little experience with themes and upgrading. I started with WordPress 2.6 or 2.7 and a slight customization to a freebie theme. When WordPress added threaded comments, they were not properly reflected in my theme, so I just took the basic crappy theme (you know: black text on a white background with that rounded blue rectangular header at the top, that screams “I did not spend any time customizing WordPress”) and played around with the CSS file until I got something resembling what you see now. Presumably, when WordPress 2.9 arrives, if there are any UI changes, I would have to do the same, which is going to suck.

I would imagine if you shelled out money for a premium theme like Thesis, then you should expect a level of quality and service such that upgrades will “just work.” But again, I have little experience in this realm and will have to yield to others’ opinions.


To reiterate what I said above, make a list of your plugins. Cross out anything that is not a must-have. You are then left with a list of “if this breaks I’m screwed” plugins. Is there anything on that list that WordPress could not do before, but now includes as integrated functionality? Do those plugins come from reliable sources or can you not tell? Perhaps stop by Beer & Blog and ask. (Ironically, I’m pimping Beer & Blog here, but have never been there myself due to my Friday schedule.) If they do come from less reliable sources, are there alternatives with similar features but do come from reliable sources?

Posted in: Code

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Brian Enigma

Brian Enigma is a Portlander, manipulator of atoms & bits, minor-league blogger, and all-around great guy. He typically writes about the interesting “maker” projects he's working on, but sometimes veers off into puzzles, software, games, local news, and current events.

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