ChangeLog:
https://chromium.googlesource.com/chromium/src/+log/52.0.2707.0..52.0.2708.0?pretty=fuller&n=10000
(Unable to narrow down the range using tools since issue is not reproducible on chromium builds)

Suspecting: r387138 ?

Kindly help to re-assign, if your changes are not cause for this issue.

I'm not sure how this got labeled Security UX, it probably needs a new component.

However, this does sound interesting to security. Chrome won't update if the system date is too far off??

+mab for his potential interest in clock things

Not my change.

This is only about the visual appearance of the "chrome://help" page, right?

@felt: HTTPS connections tend to fail if your system clock is skewed - guessing it's a symptom of that? (But should be another issue.)

ryanmyers@ - it looks like you're at least familiar with this code and recently added the error message display (https://codereview.chromium.org/1769703002) - any idea what might be up with the layout here?

Sorry, I get a HTTP 500 when I try to view the image, so I can't see what the issue is.  Reassigning to borisv, who now owns this code (I'm no longer working on Chrome).

Okay, the 500 is passing now.  It looks like a CSS issue -- the <pre> tag containing the detailed error message is wide enough that the icon is getting pushed to the side, because it's an inline-block instead of a float + clear.  The CSS for it (from src/chrome/browser/resources/help/help_content.css):

.help-page-icon {
  background-position: center;
  background-repeat: no-repeat;
  display: inline-block;
  height: 18px;
  vertical-align: middle;
  width: 18px;
}

Tweaking the CSS for the output -- either by changing help-page-icon, or by tweaking version_updater_mac.mm to put an inline style in the <pre> tag, should fix it.  In any case, it's a purely visual issue, not a functionality one.

Moving this nonessential bug to the next milestone.

For more details visit https://www.chromium.org/issue-tracking/autotriage - Your friendly Sheriffbot

This issue is Pri-1 but has already been moved once. Lowering the priority and moving to the next milestone.

For more details visit https://www.chromium.org/issue-tracking/autotriage - Your friendly Sheriffbot

Above issue is not reproducible on Latest Canary Version:55.0.2878.0 (Official Build) 6bf82374fb3a17659851bc4e830c063577ba80fd-refs/heads/master@{#422326}