Also notice the title not wrapping below the left-hand icon

This is a downgrade because the space is used far less efficiently

I'd go one step further and avoid wrapping the right-hand text

Issue title is more important than its metadata, so we absolutely shouldn't prefer wrapping it over the metadata. Especially considering that it cannot go under the metadata when wrapped

If you like the way native vertical issues look, then why not just make them always enabled? This will simplify the feature a lot

This could be the entire feature:

div[class^='IssueIndexPage-module__middlePaneGrid'] {
    container-type: inline-size;

    /* Element whose width is tracked */
    > div:not([class]) {
        max-width: 767px; /* Enable native vertical sorting */
    }
}

ul[aria-label="Drag and drop pinned issues list."] {
    flex-direction: column !important;
    width: 100cqw; /* Restore original width */
    row-gap: 0;
}

[class*="PinnedIssues-module__container"] {
    max-width: 100% !important;
    &:not(:only-child) {
        &:first-child {
            border-bottom-left-radius: 0;
            border-bottom-right-radius: 0;
        }
        &:not(:first-child, :last-child) {
            border-radius: 0;
            border-top-color: transparent;
        }
        &:last-child {
            border-top-color: transparent;
            border-top-left-radius: 0;
            border-top-right-radius: 0;
        }
    }
}

This is a downgrade

Not an upgrade:

If you look around GitHub, the style is everywhere. This is currently in my viewport alone:

It's so common even MDN has a page for it: https://developer.mozilla.org/en-US/docs/Web/CSS/How_to/Layout_cookbook/Media_objects

Issue title is more important than its metadata

Agreed, I was trying to find ways to make it look more consistent, but neither proposal is ideal.

Especially considering that it cannot go under the metadata when wrapped

I think it is possible via flex-wrap but the issue is that each row would wrap at different times, so it would look wonky with some dates on the top right, others on the bottom left.

If you like the way native vertical issues look

I only used it as an example of where the button should appear—which is also where it appears in several other GitHub components:

This could be the entire feature:

It does look good, but it's also twice as tall on desktop.

This could be the entire feature:

It does look good, but it's also twice as tall on desktop.

This is the shortest I can make it by reducing some padding:

but it still looks more noisy and wider than:

The pinned list style attempts to match the list below, which uses the same alignment: