Yahoo Mail: WTF?

This holiday season, Yahoo Mail left a big lump of coal in my stocking. Well, "coal' is a charitable way to look at it. Around two months ago, Yahoo rolled out an update of its Mail product. That's something they do every few years, and typically there's little risk because Yahoo Mail is not very good to begin with. But holy hell, this latest version is a disaster. No single metaphor does it justice. This new version is a dumpster fire that contains a tire fire tumbling off the flatbed of a train that's crashing into the Hindenburg, and rolling down a hill toward an orphanage. In other words, it's bad.

[ Disclosure section: I've been a Yahoo Mail user since the early days, and I've stuck with it for various reasons, none of them very good. All my personal mail since forever is there, and I'm lazy, and I don't like the GMail UI, and I haven't seen a compelling long-term alternative. For two years I was a Yahoo employee via their 2007 acquisition of Zimbra, and was witness to the endemic managerial and executive dysfunction that keeps them spinning their wheels. I currently work for the most recent incarnation of Zimbra, and continue to be heavily involved in implementing webmail clients. Generally I'm pretty easy-going, but the nature of my work makes webmail issues stand out. ]

You may wonder why I've waited so long to properly whine about this. There's the usual amount of laziness/busyness and more compelling things to do, but a lot of the delay is because there's a seemingly endless supply of problems to find. I kept a little list of issues, and figured after a few days I would turn it into a post. Then another serious problem cropped up, so I added it to the list. Then another. And so on. It's like one of those blowhards you run into at a party who repeats his inane points so loudly and steadily that eventually you're too tired to respond. Plus, I'm lazy about writing and end up just surfing the web (snacking on brain candy, making my mind get paunchy and out of shape) or playing some Borderlands 2.

Before I get into the boring details, I have a couple of questions that will mostly make sense to those who are familiar with the process of how software comes to market:

Yahoo Mail PM: WTF?

and

Yahoo Mail QA: WTF?

One group of people (PM, or Product Management) got paid to decide how the latest version of Yahoo Mail should look and how it should work. Then a bunch of software engineers implemented that vision. Finally, another group of people (QA, or Quality Assurance) got paid to test the new Yahoo Mail so that any issues could be resolved before release.

If it looks like I'm going easy on the engineers, you're right. I am one, so that's where my sympathies lie. They implement what PM gives them. If you adhere perfectly to a crappy blueprint while building a house, you end up with a crappy house. Also, engineers introduce bugs all the time. That's part of software development. Good engineers do less of that, but it still happens to some degree. It's up to QA to finally put the stamp of approval on a product. How they did that in this case is beyond me. In less than an hour with the new version, I found multiple issues which in my world would block the release. Then again, Yahoo Mail only has about half a billion users, so who's going to notice?

Below is a list of comments and issues about why this is the Worst Yahoo Mail Redesign Ever.

• It looks like they want to be more like GMail. They made marginal progress on that front. Mainly, they added conversations, which you old-school internet types who remember newsgroups will call "threading". So bravo for that. Seriously. I love having my mail grouped into conversations, so I no longer have to dig through my mailbox to make sure I've seen everything on a particular topic. More importantly, they preserved the Yahoo look and feel by being seriously broken in a large number of ways. Having everything suddenly become functional would have been very disorienting for their long-time users.


• The look is busy, incomplete. While I like the new trend toward flat design (as opposed to skeuomorphic, where the designer tries to make the digital version of something resemble the real thing (and now you can really impress at your next geek gathering - you're welcome)), you still have to do it right. As a whole, it looks like what happens to a page when some of the CSS doesn't load. There's no visual separation between components, and it looks like parts are missing.


• Ad display varies. There are three areas:


1. Between the search box and the mail client is a one-line ad.
2. There is sometimes an ad below the overview on the left. Sometimes not. Weird.
3. The right gutter holds the most prominent ad. Oddly, you can click a little right-pointing arrow on the right edge of the mail client and expand the mail client so that the big ad is no longer visible. When you do that, YM tries to upsell you to Yahoo Mail Plus. Fine. Dismiss that (and tell it you don't want to see it again), and the ad on the right is gone. The ad only stays gone for the current message. When you go to another message, it comes back. That's a reasonable feature compromise. If you get tired of hiding the ads, you can always use an ad blocker to hide them for you.


• If you're like me and you like to manage your Inbox by filing messages into folders (with the impossible goal of having an empty Inbox), then Yahoo Mail has long been a challenge. For one thing, I would trade all the effort of the last few redesigns for nested folders. This new version makes it even harder. Your folders are no longer directly available on the left. You must now expand a "Folders" item to see them as a list which replaces the labels of the items in the overview (my term for the left-side navigation panel). It's nice that it persists and doesn't pop down when you do something, but it leaves just the icons visible. Though the icons have helpful tooltips, it's a bit discomfiting to have the primary functions of my mailbox (composing, refreshing my Inbox) relegated to icon-only access because I want to see my folders. My guess is they did that because they want to make sure additional Yahoo functionality - Calendar, Messenger, Mobile, etc - doesn't get pushed below the fold by a long list of user folders. The last item is one they might regret: Send Feedback.


• If you select a conversation by clicking its checkbox, whatever was in the reading pane is replaced by a number telling you how many conversations (not messages) you have selected to act on. It's nice for that to be made clear, but that seems like overkill since I can lose context. Say I'm in the middle of reading a conversation in the reading pane, and I check a different conversation and mark it read using the "More" list of actions on the top toolbar. The conversation I marked read is still selected, so there's still just a "1" in the reading pane. If I uncheck that conversation, the reading pane is blank. The only way to get back to the conversation I was in the middle of reading is to start over and select it in the list view. Crud. What's worse is that the same thing happens if I right-click the conversation to mark it read. Right-click should only be a temporary contextual selection. It should not be as sticky as left-click selection.


• Conversations are not updated in-place with new messages. I was reading an active conversation with 4 messages. A new message arrived. The row for the conversation in the list had its count incremented to 5 and I saw the fragment (snippet) of the new message, but I didn't see the new message in the reading pane. Clicking the conversation in the list did not help. I had to click a different one and come back to the one I was reading to see the new message.


• They've made it easier to search your mail by adding Advanced Search. That's nice to have. The query language (for example, typing "from:bob") has been there for a while, but it's nice to give users easy access to it.


• Moving mail is awkward now that my folders aren't directly available. Drag and drop (my preferred way to file mail) still works decently, though an extra step has been introduced. You need to hover over the "Folders" entry to see your folders. The folders column is pretty skinny, so if you have named your folders in a way to get around the fact that YM has never supported nested folders (eg "business-taxes-2012" and "business-taxes-2013"), you can't tell them apart since only about the first eleven letters are visible. It gets worse if you have a lot of folders. I dragged a conversation to the Folders list, and it opened the list of folders. The folder I wanted was below the bottom, so I moved the drag icon to the bottom, expecting the folder list to scroll up so that the target folder would come into view. Instead, the conversation list scrolls. Not helpful! In fact, that's really annoying since I lose my place in my Inbox, and I have to scroll it back up to get back to where I was. The workaround is to click on Folders and scroll it down before dragging anything to it, so that the target folder is in view.


• I reverse-sorted by date to see my old mail, and now I'm really worried. My Sent folder goes back to 2000. Based on what I see, I sent one message in Dec 2000, then two in July 2003, then began a steady flow a year later in July 2004. Hmm. That doesn't sound like me. I'm generally very chatty.


• In the lower left corner, there's a little icon. Go ahead, mess with it. Try hovering over it, and then clicking it. Turns out it's for setting your background color/image. The first one is disturbingly post-apocalyptic, with some telephone poles collapsing amidst a tangle of wire in a landscape that's on fire. As far as I can tell, that's the vision that guided this redesign.


• Continuing with the lower-left weirdness, clicking to the right of that icon toggles between showing a "postcard gallery" and printing the phrase "Time for a break." Wait, what? Time for a break for whom? From what? What's the frequency?


• Okay, just a little more lower-left weirdness. Above the themes icon is one of those little nine-squares icons. It toggles a "preview" of your current list of mail, presumably with the intention of letting you test a theme before you make the agonized decision to commit to something that will take you three seconds to undo. But there's no reason to not always show that preview.


• One feature that's not new is the set of three clickable icons that appear in the right side of the From column on hover. They can be used to quickly delete a conversation, star it, or perform a search. The star is the only one that's really useful. Search is only available for single-message conversations, and it searches for other mail from the same sender, which is better than what it used to do, which was search by subject. That was useless. Delete is somewhat useful, but it takes you out of context. If I'm reading conversation A, and I move my cursor down over the delete icon for conversation B to quickly delete it, the conversation after B is loaded. That kind of defeats the purpose, in my opinion. I expected conversation A to stay. The real problem with delete is that it's easy to do accidentally when you're just trying to click on a conversation to read it. You can click anywhere in the Subject or Date column to load a conversation, but only on some variable part of the left side of the From column. So I generally try to be careful to just click the Subject.


• Finding the overview icons a bit mysterious, I wanted to quickly close the Folders panel to reveal the labels for those icons. At first I tried the things that usually work to close something transient (like a popup menu) - hitting Esc, clicking outside it. But you have to explicitly go elsewhere (like your Inbox) to get that panel to close.


• After I run a search, a panel for refining my search shows up on the left, where the Folders panel normally is. Unless I'm missing something, that means I can't drag mail from the search results into folders. Argghh. Filing mail is one of the main reasons I search. It looks like I'm doomed to use the clunky move dialog.


• Tabs are gone. Composing a new message used to happen in a separate tab, which was useful because you could flip back and forth between that and your Inbox (or whatever). The same for search results, and you used to be able to open a message into its own tab, which made it easier to multi-task. Now you have to do one thing at a time.


• The conversation view is jumbled, busy. Same things I don't like about GMail.


• Messages within a conversation other than the first and last ones are collapsed into a single row that says something like "+ 19 more messages". If multiple new messages have come into the conversation, some end up in the collapsed section, making them easy to miss. That's bad.


• Quoted text is hidden by default (good), and you can see it by clicking "Show message history". But then you can't hide it.


• Selection state is confusing. The currently displayed conversation is selected, and also the one I'm hovering over.


• Started composing a message, went to Calendar to check holiday. Calendar shows blank and hangs my browser. Only option is to kill the window and lose my composed message, at least what I've typed since the last auto-saved draft.


• Went to Contacts. Found a contact, assigned it to a list. It never takes. I can pull up the "Assign to Lists" dialog right after and the contact is not on the list. Have not found a workaround.


• Compose, drag image to compose area, send message. The image is sent as an attachment rather than as an inline image (Content-Disposition is set to "attachment" instead of "inline").


• A URL is no longer clickable. You have to copy and paste it into your browser.


• Quoted content is hidden (which is nice) and can be viewed by clicking “View message history”. But it should never hide all the content. For example, forward a message without adding any text, then view it. There is no body, just the link to view the history.


• Compose, type some stuff, then click back on Inbox to find an address you need. Guess what, your composed message is gone. If you don’t think to look in Drafts (or if it didn’t get auto-saved), you’ll have to start over.


• Read a conversation in your Inbox. On another client (eg your phone), delete it. Come back to the web client and click Inbox. Your list refreshed, but that stale conversation is still displayed, so you’re seeing content of a message that is not in your Inbox.


• Say you get a message from Ralph. The participants column shows “Ralph”. So far so good. Now begin a reply and type a letter. Wait about fifteen seconds. The text in the participants column changes to “Ralph, Me” even though you haven’t sent a reply. Your name shouldn’t be in there because you haven’t actually sent a message that is part of the conversation. All that’s happened is a draft has been auto-saved. If you cancel and then discard the draft, the column does not change and it still looks like you’re part of the conversation. An argument can be made that drafts should be part of a conversation, but I find that more confusing than helpful. It’s much cleaner to just go to the Drafts folder the few times I need to edit a draft.


• Ctrl-Enter used to be a shortcut to send the message. Now it just adds a return.


• Really bad: Went to reply to a message. Switched to plain text so that I could reply inline. Typed a paragraph. With no action on my part, my reply disappeared, so that I only saw the original, below which was a spinning circle which never went away. After a while I checked and found my reply in Drafts, but the experience was very disconcerting.


• It looks like the UI has a maximum width. If you expand your browser window laterally, the useful part stops expanding at a certain point, and the ad gutter on the right takes all the extra width.


• I was replying to a message which has an image attached. Not sure if my reply has the image, which I want it to. I scroll the conversation down so that the message at the bottom of the message I’m replying to comes into view. Then, each time I type a character, the conversation scrolls up to put my reply at the top, hiding the image.


• The browser tab title and the overview tell me I have one unread item in my Inbox, but no conversations in my Inbox are bold. If I run the search “in:inbox is:unread” I see an unread bounce notice in my Inbox. But for some reason, I can’t get it to show up no matter how much I refresh my Inbox. Hmm. I signed out and back in, and it showed up. Double Hmm.