diff --git a/CHANGELOG.md b/CHANGELOG.md
index 9691e9a160f9..9138c16e2290 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -23,6 +23,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 - Improve return value of `resolveConfig`, unwrap `ResolvableTo` ([#9972](https://github.com/tailwindlabs/tailwindcss/pull/9972))
 - Clip unbalanced brackets in arbitrary values ([#9973](https://github.com/tailwindlabs/tailwindcss/pull/9973))
 - Don’t reorder webkit scrollbar pseudo elements ([#9991](https://github.com/tailwindlabs/tailwindcss/pull/9991))
+- Deterministic sorting of arbitrary variants ([#10016](https://github.com/tailwindlabs/tailwindcss/pull/10016))
 
 ### Changed
 
diff --git a/src/lib/offsets.js b/src/lib/offsets.js
index eaa1fe6dd532..70afdb6197d3 100644
--- a/src/lib/offsets.js
+++ b/src/lib/offsets.js
@@ -1,6 +1,7 @@
 // @ts-check
 
 import bigSign from '../util/bigSign'
+import { remapBitfield } from './remap-bitfield.js'
 
 /**
  * @typedef {'base' | 'defaults' | 'components' | 'utilities' | 'variants' | 'user'} Layer
@@ -190,7 +191,7 @@ export class Offsets {
 
     return {
       ...this.create('variants'),
-      variants: 1n << this.reservedVariantBits,
+      variants: this.variantOffsets.get(variant),
     }
   }
 
@@ -243,12 +244,68 @@ export class Offsets {
     return a.index - b.index
   }
 
+  /**
+   * Arbitrary variants are recorded in the order they're encountered.
+   * This means that the order is not stable between environments and sets of content files.
+   *
+   * In order to make the order stable, we need to remap the arbitrary variant offsets to
+   * be in alphabetical order starting from the offset of the first arbitrary variant.
+   */
+  recalculateVariantOffsets() {
+    // Sort the variants by their name
+    let variants = Array.from(this.variantOffsets.entries())
+      .filter(([v]) => v.startsWith('['))
+      .sort(([a], [z]) => fastCompare(a, z))
+
+    // Sort the list of offsets
+    // This is not necessarily a discrete range of numbers which is why
+    // we're using sort instead of creating a range from min/max
+    let newOffsets = variants.map(([, offset]) => offset).sort((a, z) => bigSign(a - z))
+
+    // Create a map from the old offsets to the new offsets in the new sort order
+    /** @type {[bigint, bigint][]} */
+    let mapping = variants.map(([, oldOffset], i) => [oldOffset, newOffsets[i]])
+
+    // Remove any variants that will not move letting us skip
+    // remapping if everything happens to be in order
+    return mapping.filter(([a, z]) => a !== z)
+  }
+
+  /**
+   * @template T
+   * @param {[RuleOffset, T][]} list
+   * @returns {[RuleOffset, T][]}
+   */
+  remapArbitraryVariantOffsets(list) {
+    let mapping = this.recalculateVariantOffsets()
+
+    // No arbitrary variants? Nothing to do.
+    // Everyhing already in order? Nothing to do.
+    if (mapping.length === 0) {
+      return list
+    }
+
+    // Remap every variant offset in the list
+    return list.map((item) => {
+      let [offset, rule] = item
+
+      offset = {
+        ...offset,
+        variants: remapBitfield(offset.variants, mapping),
+      }
+
+      return [offset, rule]
+    })
+  }
+
   /**
    * @template T
    * @param {[RuleOffset, T][]} list
    * @returns {[RuleOffset, T][]}
    */
   sort(list) {
+    list = this.remapArbitraryVariantOffsets(list)
+
     return list.sort(([a], [b]) => bigSign(this.compare(a, b)))
   }
 }
@@ -268,3 +325,27 @@ function max(nums) {
 
   return max
 }
+
+/**
+ * A fast ASCII order string comparison function.
+ *
+ * Using `.sort()` without a custom compare function is faster
+ * But you can only use that if you're sorting an array of
+ * only strings. If you're sorting strings inside objects
+ * or arrays, you need must use a custom compare function.
+ *
+ * @param {string} a
+ * @param {string} b
+ */
+function fastCompare(a, b) {
+  let aLen = a.length
+  let bLen = b.length
+  let minLen = aLen < bLen ? aLen : bLen
+
+  for (let i = 0; i < minLen; i++) {
+    let cmp = a.charCodeAt(i) - b.charCodeAt(i)
+    if (cmp !== 0) return cmp
+  }
+
+  return aLen - bLen
+}
diff --git a/src/lib/remap-bitfield.js b/src/lib/remap-bitfield.js
new file mode 100644
index 000000000000..3ddaf20234c4
--- /dev/null
+++ b/src/lib/remap-bitfield.js
@@ -0,0 +1,82 @@
+// @ts-check
+
+/**
+ * We must remap all the old bits to new bits for each set variant
+ * Only arbitrary variants are considered as those are the only
+ * ones that need to be re-sorted at this time
+ *
+ * An iterated process that removes and sets individual bits simultaneously
+ * will not work because we may have a new bit that is also a later old bit
+ * This means that we would be removing a previously set bit which we don't
+ * want to do
+ *
+ * For example (assume `bN` = `1<<N`)
+ * Given the "total" mapping `[[b1, b3], [b2, b4], [b3, b1], [b4, b2]]`
+ * The mapping is "total" because:
+ * 1. Every input and output is accounted for
+ * 2. All combinations are unique
+ * 3. No one input maps to multiple outputs and vice versa
+ * And, given an offset with all bits set:
+ * V = b1 | b2 | b3 | b4
+ *
+ * Let's explore the issue with removing and setting bits simultaneously:
+ * V & ~b1 | b3 = b2 | b3 | b4
+ * V & ~b2 | b4 = b3 | b4
+ * V & ~b3 | b1 = b1 | b4
+ * V & ~b4 | b2 = b1 | b2
+ *
+ * As you can see, we end up with the wrong result.
+ * This is because we're removing a bit that was previously set.
+ * And, thus the final result is missing b3 and b4.
+ *
+ * Now, let's explore the issue with removing the bits first:
+ * V & ~b1 = b2 | b3 | b4
+ * V & ~b2 = b3 | b4
+ * V & ~b3 = b4
+ * V & ~b4 = 0
+ *
+ * And then setting the bits:
+ * V | b3 = b3
+ * V | b4 = b3 | b4
+ * V | b1 = b1 | b3 | b4
+ * V | b2 = b1 | b2 | b3 | b4
+ *
+ * We get the correct result because we're not removing any bits that were
+ * previously set thus properly remapping the bits to the new order
+ *
+ * To collect this into a single operation that can be done simultaneously
+ * we must first create a mask for the old bits that are set and a mask for
+ * the new bits that are set. Then we can remove the old bits and set the new
+ * bits simultaneously in a "single" operation like so:
+ * OldMask = b1 | b2 | b3 | b4
+ * NewMask = b3 | b4 | b1 | b2
+ *
+ * So this:
+ * V & ~oldMask | newMask
+ *
+ * Expands to this:
+ * V & ~b1 & ~b2 & ~b3 & ~b4 | b3 | b4 | b1 | b2
+ *
+ * Which becomes this:
+ * b1 | b2 | b3 | b4
+ *
+ * Which is the correct result!
+ *
+ * @param {bigint} num
+ * @param {[bigint, bigint][]} mapping
+ */
+export function remapBitfield(num, mapping) {
+  // Create masks for the old and new bits that are set
+  let oldMask = 0n
+  let newMask = 0n
+  for (let [oldBit, newBit] of mapping) {
+    if (num & oldBit) {
+      oldMask = oldMask | oldBit
+      newMask = newMask | newBit
+    }
+  }
+
+  // Remove all old bits
+  // Set all new bits
+  return (num & ~oldMask) | newMask
+}
diff --git a/tests/arbitrary-variants.test.js b/tests/arbitrary-variants.test.js
index 3f8f8b81ff91..f51b20272b4d 100644
--- a/tests/arbitrary-variants.test.js
+++ b/tests/arbitrary-variants.test.js
@@ -517,11 +517,11 @@ test('allows attribute variants with quotes', () => {
     expect(result.css).toMatchFormattedCss(css`
       ${defaults}
 
-      .\[\&\[data-test\=\'2\'\]\]\:underline[data-test="2"] {
+      .\[\&\[data-test\=\"2\"\]\]\:underline[data-test='2'] {
         text-decoration-line: underline;
       }
 
-      .\[\&\[data-test\=\"2\"\]\]\:underline[data-test='2'] {
+      .\[\&\[data-test\=\'2\'\]\]\:underline[data-test='2'] {
         text-decoration-line: underline;
       }
     `)
@@ -554,12 +554,12 @@ test('classes in arbitrary variants should not be prefixed', () => {
 
   return run(input, config).then((result) => {
     expect(result.css).toMatchFormattedCss(css`
-      .foo .\[\.foo_\&\]\:tw-text-red-400 {
+      .\[\&_\.foo\]\:tw-text-red-400 .foo {
         --tw-text-opacity: 1;
         color: rgb(248 113 113 / var(--tw-text-opacity));
       }
 
-      .\[\&_\.foo\]\:tw-text-red-400 .foo {
+      .foo .\[\.foo_\&\]\:tw-text-red-400 {
         --tw-text-opacity: 1;
         color: rgb(248 113 113 / var(--tw-text-opacity));
       }
@@ -593,22 +593,22 @@ test('classes in the same arbitrary variant should not be prefixed', () => {
 
   return run(input, config).then((result) => {
     expect(result.css).toMatchFormattedCss(css`
-      .foo .\[\.foo_\&\]\:tw-bg-white {
+      .\[\&_\.foo\]\:tw-bg-white .foo {
         --tw-bg-opacity: 1;
         background-color: rgb(255 255 255 / var(--tw-bg-opacity));
       }
 
-      .foo .\[\.foo_\&\]\:tw-text-red-400 {
+      .\[\&_\.foo\]\:tw-text-red-400 .foo {
         --tw-text-opacity: 1;
         color: rgb(248 113 113 / var(--tw-text-opacity));
       }
 
-      .\[\&_\.foo\]\:tw-bg-white .foo {
+      .foo .\[\.foo_\&\]\:tw-bg-white {
         --tw-bg-opacity: 1;
         background-color: rgb(255 255 255 / var(--tw-bg-opacity));
       }
 
-      .\[\&_\.foo\]\:tw-text-red-400 .foo {
+      .foo .\[\.foo_\&\]\:tw-text-red-400 {
         --tw-text-opacity: 1;
         color: rgb(248 113 113 / var(--tw-text-opacity));
       }
@@ -1063,3 +1063,39 @@ it('should be possible to use modifiers and arbitrary peers', () => {
     `)
   })
 })
+
+it('Arbitrary variants are ordered alphabetically', () => {
+  let config = {
+    content: [
+      {
+        raw: html`
+          <div>
+            <div class="[&::b]:underline"></div>
+            <div class="[&::a]:underline"></div>
+            <div class="[&::c]:underline"></div>
+            <div class="[&::b]:underline"></div>
+          </div>
+        `,
+      },
+    ],
+    corePlugins: { preflight: false },
+  }
+
+  let input = css`
+    @tailwind utilities;
+  `
+
+  return run(input, config).then((result) => {
+    expect(result.css).toMatchFormattedCss(css`
+      .\[\&\:\:a\]\:underline::a {
+        text-decoration-line: underline;
+      }
+      .\[\&\:\:b\]\:underline::b {
+        text-decoration-line: underline;
+      }
+      .\[\&\:\:c\]\:underline::c {
+        text-decoration-line: underline;
+      }
+    `)
+  })
+})
diff --git a/tests/variants.test.js b/tests/variants.test.js
index d6022b8675ab..33b5d2ffe899 100644
--- a/tests/variants.test.js
+++ b/tests/variants.test.js
@@ -1122,25 +1122,25 @@ test('arbitrary variant selectors should not re-order scrollbar pseudo classes',
   let result = await run(input, config)
 
   expect(result.css).toMatchFormattedCss(css`
-    .\[\&\:\:-webkit-scrollbar\:hover\]\:underline::-webkit-scrollbar:hover {
+    .\[\&\:\:-webkit-resizer\:hover\]\:underline::-webkit-resizer:hover {
       text-decoration-line: underline;
     }
     .\[\&\:\:-webkit-scrollbar-button\:hover\]\:underline::-webkit-scrollbar-button:hover {
       text-decoration-line: underline;
     }
-    .\[\&\:\:-webkit-scrollbar-thumb\:hover\]\:underline::-webkit-scrollbar-thumb:hover {
+    .\[\&\:\:-webkit-scrollbar-corner\:hover\]\:underline::-webkit-scrollbar-corner:hover {
       text-decoration-line: underline;
     }
-    .\[\&\:\:-webkit-scrollbar-track\:hover\]\:underline::-webkit-scrollbar-track:hover {
+    .\[\&\:\:-webkit-scrollbar-thumb\:hover\]\:underline::-webkit-scrollbar-thumb:hover {
       text-decoration-line: underline;
     }
     .\[\&\:\:-webkit-scrollbar-track-piece\:hover\]\:underline::-webkit-scrollbar-track-piece:hover {
       text-decoration-line: underline;
     }
-    .\[\&\:\:-webkit-scrollbar-corner\:hover\]\:underline::-webkit-scrollbar-corner:hover {
+    .\[\&\:\:-webkit-scrollbar-track\:hover\]\:underline::-webkit-scrollbar-track:hover {
       text-decoration-line: underline;
     }
-    .\[\&\:\:-webkit-resizer\:hover\]\:underline::-webkit-resizer:hover {
+    .\[\&\:\:-webkit-scrollbar\:hover\]\:underline::-webkit-scrollbar:hover {
       text-decoration-line: underline;
     }
   `)