diff --git a/packages/less/lib/less/tree/nested-at-rule.js b/packages/less/lib/less/tree/nested-at-rule.js
index 4d3860839..6eab3339d 100644
--- a/packages/less/lib/less/tree/nested-at-rule.js
+++ b/packages/less/lib/less/tree/nested-at-rule.js
@@ -37,6 +37,40 @@ import Node from './node.js';
  * }} NestableAtRuleThis
  */
 
+// A media query may only carry a media type at its front, before any
+// conditions (https://drafts.csswg.org/mediaqueries-5/#typedef-media-query-list).
+// Operators that join media-query parts, so a fragment leading with one is not
+// a media type. Any other bare identifier is treated as a type, since unknown
+// media types are valid non-matches in CSS, not syntax errors.
+const MEDIA_QUERY_OPERATORS = ['and', 'or'];
+
+/**
+ * Whether a flattened media-query fragment leads with a media type, e.g.
+ * `screen`, `only screen`, `print and (color)` or an unknown type like `foo`.
+ * @param {Node & { value?: * }} fragment
+ */
+function startsWithMediaType(fragment) {
+    let head;
+    if (fragment.type === 'Keyword' || fragment.type === 'Anonymous') {
+        head = fragment.value;
+    } else if (fragment.type === 'Expression' && Array.isArray(fragment.value)) {
+        const parts = fragment.value.filter(p => p && p.value !== undefined);
+        let idx = 0;
+        const first = parts[idx] && String(parts[idx].value).toLowerCase();
+        if (first === 'not' || first === 'only') { idx++; }
+        head = parts[idx] && parts[idx].value;
+    }
+    if (typeof head !== 'string' || head === '') {
+        return false;
+    }
+    // Inspect only the first token. A media type is a bare identifier; a feature
+    // condition begins with '(' - e.g. an escaped ~"(max-width: 1px)" is an
+    // Anonymous whose whole value is "(max-width: 1px)", which is not a media type.
+    const firstToken = head.trim().split(/[\s(]/)[0];
+    return firstToken !== ''
+        && MEDIA_QUERY_OPERATORS.indexOf(firstToken.toLowerCase()) < 0;
+}
+
 const NestableAtRulePrototype = {
 
     isRulesetLike() {
@@ -149,6 +183,13 @@ const NestableAtRulePrototype = {
                 /** @param {Node & { toCSS?: Function }} fragment */
                     fragment => fragment.toCSS ? fragment : new Anonymous(/** @type {string} */ (/** @type {unknown} */ (fragment))));
 
+                // A media type nested inside conditions must move ahead of them
+                // so the flattened query stays valid (issue #3694, #3764).
+                const types = /** @type {Node[]} */ (path).filter(startsWithMediaType);
+                if (types.length && types.length < /** @type {Node[]} */ (path).length) {
+                    path = types.concat(/** @type {Node[]} */ (path).filter(f => !startsWithMediaType(f)));
+                }
+
                 for (i = /** @type {Node[]} */ (path).length - 1; i > 0; i--) {
                 /** @type {Node[]} */ (path).splice(i, 0, new Anonymous('and'));
                 }
diff --git a/packages/test-data/tests-unit/media-nested-type/media-nested-type.css b/packages/test-data/tests-unit/media-nested-type/media-nested-type.css
new file mode 100644
index 000000000..adec56722
--- /dev/null
+++ b/packages/test-data/tests-unit/media-nested-type/media-nested-type.css
@@ -0,0 +1,40 @@
+@media screen and (max-width: 500px) {
+  .a {
+    color: red;
+  }
+}
+@media only screen and (min-width: 100px) {
+  .b {
+    color: blue;
+  }
+}
+@media all and (max-width: 9px) {
+  .c {
+    color: green;
+  }
+}
+@media print and (color) and (min-width: 1px) {
+  .d {
+    color: black;
+  }
+}
+@media screen and (max-width: 500px) {
+  .e {
+    color: red;
+  }
+}
+@media (max-width: 500px) and (min-width: 100px) {
+  .f {
+    color: red;
+  }
+}
+@media tester and (max-width: 500px) {
+  .g {
+    color: red;
+  }
+}
+@media screen and (max-width: 500px) {
+  .h {
+    color: red;
+  }
+}
diff --git a/packages/test-data/tests-unit/media-nested-type/media-nested-type.less b/packages/test-data/tests-unit/media-nested-type/media-nested-type.less
new file mode 100644
index 000000000..df9b62a35
--- /dev/null
+++ b/packages/test-data/tests-unit/media-nested-type/media-nested-type.less
@@ -0,0 +1,51 @@
+// A media type nested inside conditions must lead the flattened query,
+// otherwise the result is invalid CSS (issue #3694, #3764).
+@media (max-width: 500px) {
+  @media screen {
+    .a { color: red; }
+  }
+}
+@media (min-width: 100px) {
+  @media only screen {
+    .b { color: blue; }
+  }
+}
+@media (max-width: 9px) {
+  @media all {
+    .c { color: green; }
+  }
+}
+@media (min-width: 1px) {
+  @media print and (color) {
+    .d { color: black; }
+  }
+}
+
+// Already-correct ordering is preserved.
+@media screen {
+  @media (max-width: 500px) {
+    .e { color: red; }
+  }
+}
+
+// Queries without a media type are left untouched.
+@media (max-width: 500px) {
+  @media (min-width: 100px) {
+    .f { color: red; }
+  }
+}
+
+// Unknown media types are valid CSS non-matches, so they reorder too.
+@media (max-width: 500px) {
+  @media tester {
+    .g { color: red; }
+  }
+}
+
+// An escaped-string feature condition (Anonymous) must not be mistaken for a media type.
+@fc: ~"(max-width: 500px)";
+@media @fc {
+  @media screen {
+    .h { color: red; }
+  }
+}