Word wrap with css `hyphens` fails to wrap substring

Question

I recently switched from overflow-wrap to hyphens for breaking text between lines. However, I have encountered a case that seemingly fails to hyphenate any words before a certain substring. I am at a loss as to why this could be.

Observe the gif below, the full string to be displayed is /people/type:astronauts/name-gregory-chamitoff/profile however when the width is less than about 210px none of the words in the substring /people/type:astronauts/name- are ever hyphenated and pushed to the next line. But, longer that 210px the hyphenation works fine. It's almost like it's treating this substring as a continuous word.

.test {
  font-size: 20px;
  width: 210px;
  /* adding this works but defeats the use of hyphens
  overflow-wrap: break-word;
  */
  hyphens: auto;
  overflow: hidden;
  background-color: white;
}

html {
  background-color: black;
}

<div class="test">/people/type:astronauts/name-gregory-chamitoff/profile</div>

The only thing I have found that fixes this is to use something like that below as a catch-all. This is great however, it does not prioritize hyphenating over breaking of the words. I am looking for other solutions than this that makes hyphens work for all or most strings, or even this one case!

.test {
  overflow-wrap: break-word;
  word-wrap: break-word;
  word-break: break-all;
  word-break: break-word;
  hyphens: auto;
}

Answer 1

As @Salman A has pointed out, quite a lot of characters (e.g like slashes or colons, undescores etc.) are not recognized as proper word/syllable joints. Strings like "chamitoff/profile" will be treated as one long compound word "chamitoffprofile".

When it comes to URL like strings, you don't want to overflow – you'd still be better off with something like word-break: break-word;

Speaking of css hyphens property: its capabilities are still 'limited' (at least in 2021). E.g. Chrome has introduced support for this feature in version 88 (according to caniuse).

Here's a resizable snippet:

*{
box-sizing:border-box;
}

body{
font-family: 'Segoe UI';
font-size: calc(1.75vw + 1.75vh / 2);
padding: 10px;
}

.resizable{
  width: 20ch;
  height: 10em;
  hyphens: auto;
  resize:both;
  overflow:auto;
  padding-right:1em;
  border: 1px solid #ccc
}

.resizable p{
  hyphens: auto;
}

.break-words{
  hyphens: none;
  word-break: break-word;
}

 <h2>Example</h2>
 <div class="resizable">
    <p>people/type:astronauts/name-gregory-chamitoff/profile <br /><strong>Original</strong></p>
    <p>peopletype:astronautsname-gregory-chamitoffprofile <br /><strong>Dash replaced by hyphens</strong></p>
    <p>peopletype_astronautsname_gregory_chamitoff_profile <br /><strong>Dash replaced by underscores</strong></p>
    <p>peopletype astronautsname-gregory-chamitoffprofile <br /><strong>Dash and colons replaced by hyphens</strong></p>
    <p>peopletype astronauts name gregory chamitoff profile <br /><strong>Dash replaced by spaces</strong></p>
    <p class="break-words">people/type:astronauts/name-gregory-chamitoff/profile <br /><strong>Dash replaced by spaces</strong></p>
   </div>

<h2>URLs</h2>
   <div class="resizable">
       <p><a href="#">https://www.maybeweshouldhaveoptedfor ashorterdomain.com/contact/specialinterest?product_id=1234567878</a> <br /><strong>URL – "hyphenated"</strong></p>

      <p class="break-words"><a href="#">https://www.maybeweshouldhaveoptedfor ashorterdomain.com/contact/specialinterest?product_id=1234567878</a> <br /><strong>URL – word-break</strong></p>
      <p class="break-words"><a href="#">contact@maybeweshouldhaveoptedfor ashorterdomain.com</a> <br /><strong>Email example</strong></p>
  </div>

Unless browsers/css-implementations widely support improved hyphenation concepts like hyphenate-limit-chars (... formerly existent) or hyphenation exception rules you should really curb your enthusiasm.

Conclusion
(2021 – hopefully we'll see improvements the next years)
You still have to choose between an imperfect 'brute-force' method like word-break – at least preventing undesired overflows and an inelaborate (... to be very polite) css based hyphenation property/feature that's still missing any mandatory fine grained controls.

Answer 2

I am not sure if it is what are you looking for:

.test {
    hyphens: auto;
    color:white;
  }
  html {
    background-color: black;
  }

<!DOCTYPE html>
<html lang="en">
<head>
    <meta charset="UTF-8">
    <meta http-equiv="X-UA-Compatible" content="IE=edge">
    <meta name="viewport" content="width=device-width, initial-scale=1.0">
    <title>Document</title>
    <link rel="stylesheet" href="style.css">
</head>
<body >
    <div class="test">/people/type:&shyastronauts/&shyname-gregory-chamitoff/profile here i have another words</div>
</body>
</html>