diff --git a/changelog_unreleased/css/16907.md b/changelog_unreleased/css/16907.md
new file mode 100644
index 000000000..a8c0a79bf
--- /dev/null
+++ b/changelog_unreleased/css/16907.md
@@ -0,0 +1,28 @@
+#### Break before breaking comma separated values (#16907 by @seiyab)
+
+<!-- prettier-ignore -->
+```css
+/* Input */
+a {
+  background-image:
+    linear-gradient(to bottom, rgb(255 255 0 / 50%), rgb(0 0 255 / 50%)),
+    url("catfront.png");
+}
+
+/* Prettier stable */
+a {
+  background-image: linear-gradient(
+      to bottom,
+      rgb(255 255 0 / 50%),
+      rgb(0 0 255 / 50%)
+    ),
+    url("catfront.png");
+}
+
+/* Prettier main */
+a {
+  background-image:
+    linear-gradient(to bottom, rgb(255 255 0 / 50%), rgb(0 0 255 / 50%)),
+    url("catfront.png");
+}
+```
diff --git a/src/language-css/print/parenthesized-value-group.js b/src/language-css/print/parenthesized-value-group.js
index 58bec9ed2..197b55fb3 100644
--- a/src/language-css/print/parenthesized-value-group.js
+++ b/src/language-css/print/parenthesized-value-group.js
@@ -88,7 +88,11 @@ function printParenthesizedValueGroup(path, options, print) {
     assertDocArray(groupDocs);
     const withComma = chunk(join(",", groupDocs), 2);
     const parts = join(forceHardLine ? hardline : line, withComma);
-    return indent(forceHardLine ? [hardline, parts] : group(fill(parts)));
+    return indent(
+      forceHardLine
+        ? [hardline, parts]
+        : group([shouldPrecededBySoftline(path) ? softline : "", fill(parts)]),
+    );
   }
 
   const parts = path.map(({ node: child, isLast, index }) => {
@@ -165,6 +169,15 @@ function shouldBreakList(path) {
   );
 }
 
+function shouldPrecededBySoftline(path) {
+  return path.match(
+    (node) => node.type === "value-paren_group" && !node.open,
+    (node, key) => key === "group" && node.type === "value-value",
+    (node, key) => key === "group" && node.type === "value-root",
+    (node, key) => key === "value" && node.type === "css-decl",
+  );
+}
+
 /**
  * @template {*} T
  * @param {T[]} array
diff --git a/tests/format/markdown/code/__snapshots__/format.test.js.snap b/tests/format/markdown/code/__snapshots__/format.test.js.snap
index a9af95113..b3ac1d86f 100644
--- a/tests/format/markdown/code/__snapshots__/format.test.js.snap
+++ b/tests/format/markdown/code/__snapshots__/format.test.js.snap
@@ -412,11 +412,8 @@ background-image: linear-gradient(
 
 =====================================output=====================================
 \`\`\`css
-background-image: linear-gradient(
-    to bottom,
-    rgb(255 255 0 / 50%),
-    rgb(0 0 255 / 50%)
-  ),
+background-image:
+  linear-gradient(to bottom, rgb(255 255 0 / 50%), rgb(0 0 255 / 50%)),
   url("catfront.png");
 \`\`\`
 
@@ -452,7 +449,8 @@ width: 400px;
 .box {
   margin: 10px 0;
   color: #fff;
-  background: linear-gradient(
+  background:
+    linear-gradient(
       90deg,
       rgb(131 58 180 / 100%) 0%,
       rgb(253 29 29 / 60%) 60%,
@@ -498,7 +496,8 @@ background-position:
 .multi-bg-example {
   width: 100%;
   height: 400px;
-  background-image: url(firefox.png), url(bubbles.png),
+  background-image:
+    url(firefox.png), url(bubbles.png),
     linear-gradient(to right, rgb(30 75 115 / 100%), rgb(255 255 255 / 0%));
   background-repeat: no-repeat, no-repeat, no-repeat;
   background-position:
@@ -535,11 +534,8 @@ proseWrap: "always"
 =====================================output=====================================
 \`\`\`css
 .stacked-linear {
-  background: linear-gradient(
-      217deg,
-      rgb(255 0 0 / 80%),
-      rgb(255 0 0 / 0%) 70.71%
-    ),
+  background:
+    linear-gradient(217deg, rgb(255 0 0 / 80%), rgb(255 0 0 / 0%) 70.71%),
     linear-gradient(127deg, rgb(0 255 0 / 80%), rgb(0 255 0 / 0%) 70.71%),
     linear-gradient(336deg, rgb(0 0 255 / 80%), rgb(0 0 255 / 0%) 70.71%);
 }
@@ -648,7 +644,8 @@ rgb(255 255 0 / 50%) 120px,
 =====================================output=====================================
 \`\`\`css
 .multi-repeating-linear {
-  background: repeating-linear-gradient(
+  background:
+    repeating-linear-gradient(
       190deg,
       rgb(255 0 0 / 50%) 40px,
       rgb(255 153 0 / 50%) 80px,
@@ -765,7 +762,8 @@ transparent 69px,
 =====================================output=====================================
 \`\`\`css
 .plaid-gradient {
-  background: repeating-linear-gradient(
+  background:
+    repeating-linear-gradient(
       90deg,
       transparent,
       transparent 50px,
@@ -810,7 +808,8 @@ transparent 69px,
       rgb(143 77 63 / 25%) 10px
     );
 
-  background: repeating-linear-gradient(
+  background:
+    repeating-linear-gradient(
       90deg,
       transparent 0 50px,
       rgb(255 127 0 / 25%) 50px 56px,
@@ -1110,8 +1109,8 @@ mask-image: image(url(mask.png), skyblue),                          linear-gradi
 =====================================output=====================================
 \`\`\`css
 /* Multiple values */
-mask-image: image(url(mask.png), skyblue),
-  linear-gradient(rgb(0 0 0 / 100%), transparent);
+mask-image:
+  image(url(mask.png), skyblue), linear-gradient(rgb(0 0 0 / 100%), transparent);
 \`\`\`
 
 ================================================================================
@@ -1269,9 +1268,10 @@ U+0152-0153, U+02BB-02BC, U+02C6,
       local("Montserrat Regular"),
       local("Montserrat-Regular"),
       url("fonts/montserrat-regular.woff2") format("woff2");
-    unicode-range: U+0000-00FF, U+0131, U+0152-0153, U+02BB-02BC, U+02C6,
-      U+02DA, U+02DC, U+2000-206F, U+2074, U+20AC, U+2122, U+2191, U+2193,
-      U+2212, U+2215, U+FEFF, U+FFFD;
+    unicode-range:
+      U+0000-00FF, U+0131, U+0152-0153, U+02BB-02BC, U+02C6, U+02DA, U+02DC,
+      U+2000-206F, U+2074, U+20AC, U+2122, U+2191, U+2193, U+2212, U+2215,
+      U+FEFF, U+FFFD;
   }
 }
 \`\`\`