diff --git a/packages/cms/src/ui.js b/packages/cms/src/ui.js
index 6b276d43130..4063a97f6d2 100644
--- a/packages/cms/src/ui.js
+++ b/packages/cms/src/ui.js
@@ -66,6 +66,7 @@ export const {
     ListingToggleAll,
     LivePreview,
     LivePreviewPopout,
+    MiddleEllipsis,
     Modal,
     ModalClose,
     ModalTitle,
diff --git a/resources/css/components/assets.css b/resources/css/components/assets.css
index 248c2d9efe1..d1a1b7cee4e 100644
--- a/resources/css/components/assets.css
+++ b/resources/css/components/assets.css
@@ -120,7 +120,7 @@
     grid-template-columns: repeat(auto-fill, minmax(80px, 1fr));
 
     [data-placeholder-shown] {
-        @apply overflow-hidden mt-2 text-center font-mono text-xs text-ellipsis whitespace-nowrap lowercase;
+        @apply overflow-hidden mt-2 text-center text-xs text-ellipsis whitespace-nowrap lowercase;
         &:has(+ .st-has-error) {
             @apply text-red-600 dark:text-red-500;
         }
@@ -158,7 +158,8 @@
 }
 
 .asset-filename {
-    @apply font-mono text-xs text-gray-500 dark:text-gray-300 mt-2 whitespace-nowrap text-center;
+    @apply text-xs text-gray-500 dark:text-gray-300 mt-2 whitespace-nowrap text-center st-text-legibility;
+    font-variant: tabular-nums; /* Disable common-ligatures from body default */
     .selected & {
         @apply text-blue-500;
         .dark & {
diff --git a/resources/js/bootstrap/cms/ui.js b/resources/js/bootstrap/cms/ui.js
index adf68ff74ce..28803da78b0 100644
--- a/resources/js/bootstrap/cms/ui.js
+++ b/resources/js/bootstrap/cms/ui.js
@@ -66,6 +66,7 @@ export {
     ListingToggleAll,
     LivePreview,
     LivePreviewPopout,
+    MiddleEllipsis,
     Modal,
     ModalClose,
     ModalTitle,
diff --git a/resources/js/components/assets/Browser/Grid.vue b/resources/js/components/assets/Browser/Grid.vue
index c3513ce3fd7..a58c9dcf7c3 100644
--- a/resources/js/components/assets/Browser/Grid.vue
+++ b/resources/js/components/assets/Browser/Grid.vue
@@ -37,7 +37,7 @@
                             <button @click="selectFolder(folder.path)" class="group h-[66px] w-[80px]">
                                 <FolderSvg class="size-full text-blue-400/90 hover:text-blue-400" />
                                 <div
-                                    class="overflow-hidden mt-2 text-center font-mono text-xs text-ellipsis whitespace-nowrap text-gray-500 dark:text-gray-300"
+                                    class="overflow-hidden mt-2 text-center text-xs text-ellipsis whitespace-nowrap text-gray-500 dark:text-gray-300"
                                     v-text="folder.basename"
                                     :title="folder.basename"
                                 />
@@ -67,7 +67,7 @@
                         submit-mode="enter"
                         :placeholder="__('Name')"
                         :class="[
-                            'flex w-[80px] items-center placeholder:lowercase justify-center overflow-hidden mt-2 text-center font-mono text-xs text-ellipsis whitespace-nowrap placeholder:text-gray-400 dark:placeholder:text-gray-500 text-gray-500',
+                            'flex w-[80px] items-center placeholder:lowercase justify-center overflow-hidden mt-2 text-center text-xs text-ellipsis whitespace-nowrap placeholder:text-gray-400 dark:placeholder:text-gray-500 text-gray-500',
                             { 'st-has-error': creatingFolderError }
                         ]"
                         @submit="$emit('create-folder', newFolderName)"
@@ -168,7 +168,9 @@
                         </ContextMenu>
                     </Context>
                 </ItemActions>
-                <div class="asset-filename" v-text="truncateFilename(asset.basename)" :title="asset.basename" />
+                <div class="asset-filename">
+                    <MiddleEllipsis :text="asset.basename" />
+                </div>
             </div>
         </section>
 
@@ -193,7 +195,8 @@ import {
     DropdownMenu,
     DropdownLabel,
     DropdownItem,
-    DropdownSeparator
+    DropdownSeparator,
+    MiddleEllipsis
 } from '@ui';
 import { injectListingContext } from '@/components/ui/Listing/Listing.vue';
 import ItemActions from '@/components/actions/ItemActions.vue';
@@ -217,6 +220,7 @@ export default {
         DropdownSeparator,
         ItemActions,
         FolderSvg,
+        MiddleEllipsis,
     },
 
     props: {
@@ -245,17 +249,6 @@ export default {
     },
 
     methods: {
-        truncateFilename(filename) {
-            const maxLength = Math.floor(this.thumbnailSize / 7);
-            if (filename.length <= maxLength) return filename;
-
-            const extension = filename.split('.').pop();
-            const name = filename.slice(0, -(extension.length + 1));
-            const charsToKeep = Math.floor((maxLength - 3 - extension.length) / 2);
-
-            return `${name.slice(0, charsToKeep)}…${name.slice(-charsToKeep)}.${extension}`;
-        },
-
         isSelected(id) {
             return this.selectedAssets.includes(id);
         },
diff --git a/resources/js/components/ui/MiddleEllipsis/MiddleEllipsis.vue b/resources/js/components/ui/MiddleEllipsis/MiddleEllipsis.vue
new file mode 100644
index 00000000000..8eb1c7278d2
--- /dev/null
+++ b/resources/js/components/ui/MiddleEllipsis/MiddleEllipsis.vue
@@ -0,0 +1,34 @@
+<script setup>
+import { ref, onMounted, onUnmounted, watch } from 'vue';
+import truncateOnResize from './TruncateText.js';
+
+const props = defineProps({
+    text: { type: String, required: true },
+});
+
+const truncatedRef = ref(null);
+let cleanup = null;
+
+const bindTruncation = () => {
+    if (!truncatedRef.value) {
+        return;
+    }
+
+    cleanup?.();
+    cleanup = truncateOnResize(truncatedRef.value, props.text);
+};
+
+onMounted(bindTruncation);
+
+watch(() => props.text, bindTruncation);
+
+onUnmounted(() => {
+    cleanup?.();
+});
+</script>
+
+<template>
+    <div class="relative">
+        <div ref="truncatedRef" v-text="text" :title="text" :aria-label="text"></div>
+    </div>
+</template>
diff --git a/resources/js/components/ui/MiddleEllipsis/TruncateText.js b/resources/js/components/ui/MiddleEllipsis/TruncateText.js
new file mode 100644
index 00000000000..1581526a0f1
--- /dev/null
+++ b/resources/js/components/ui/MiddleEllipsis/TruncateText.js
@@ -0,0 +1,89 @@
+import characterWidths from './TruncateTextCharacterMap.js';
+
+const BASE_FONT_SIZE = 16;
+
+/**
+ * Observes the parent element for resize events and truncates the text
+ * with a middle ellipsis when it overflows.
+ *
+ * Returns a cleanup function to disconnect the observer.
+ */
+export default function truncateOnResize(element, text, { ellipsis = '...' } = {}) {
+    if (!element.offsetParent || !text) {
+        return () => {};
+    }
+
+    const observer = new ResizeObserver(() => {
+        element.textContent = middleTruncate(element, text, ellipsis);
+    });
+
+    observer.observe(element.offsetParent);
+
+    return () => observer.disconnect();
+}
+
+/**
+ * Truncates text from the middle when it's too wide for the element,
+ * preserving the start and end of the string for readability.
+ */
+function middleTruncate(element, text, ellipsis) {
+    const style = window.getComputedStyle(element);
+    const fontSize = Number.parseFloat(style.fontSize);
+    const fontFamily = normalizeFontFamily(style.fontFamily.split(',')[0]);
+
+    const availableWidth = measureAvailableWidth(element);
+
+    if (measureTextWidth(text, fontFamily, fontSize) <= availableWidth) {
+        return text;
+    }
+
+    let remainingWidth = availableWidth - measureTextWidth(ellipsis, fontFamily, fontSize);
+    let start = '';
+    let end = '';
+
+    // Build the truncated string from both ends, one character at a time,
+    // until we run out of space.
+    for (let i = 0; i < Math.floor(text.length / 2); i++) {
+        const startChar = text[i];
+        remainingWidth -= measureCharWidth(startChar, fontFamily, fontSize);
+        if (remainingWidth < 0) break;
+        start += startChar;
+
+        const endChar = text[text.length - i - 1];
+        remainingWidth -= measureCharWidth(endChar, fontFamily, fontSize);
+        if (remainingWidth < 0) break;
+        end = endChar + end;
+    }
+
+    return start + ellipsis + end;
+}
+
+// -- Text width estimation ------------------------------------------------
+// Uses a precomputed character width map (at 16px base size) to estimate
+// text width without triggering DOM layout. Unmapped characters fall back
+// to 'W' width (the widest common character) for a safe overestimate.
+
+function measureCharWidth(char, fontFamily, fontSize) {
+    const widths = characterWidths[fontFamily] ?? {};
+    const baseWidth = widths[char] ?? widths.W ?? BASE_FONT_SIZE;
+    return baseWidth * (fontSize / BASE_FONT_SIZE);
+}
+
+function normalizeFontFamily(fontFamily) {
+    return fontFamily.replaceAll('"', '').replaceAll("'", '').trim().toLowerCase();
+}
+
+function measureTextWidth(text, fontFamily, fontSize) {
+    let width = 0;
+    for (const char of text) {
+        width += measureCharWidth(char, fontFamily, fontSize);
+    }
+    return width;
+}
+
+function measureAvailableWidth(element) {
+    const parent = element.parentElement;
+    if (!parent) return 0;
+
+    return Number.parseFloat(window.getComputedStyle(parent).width);
+}
diff --git a/resources/js/components/ui/MiddleEllipsis/TruncateTextCharacterMap.js b/resources/js/components/ui/MiddleEllipsis/TruncateTextCharacterMap.js
new file mode 100644
index 00000000000..75d2b0c0e1a
--- /dev/null
+++ b/resources/js/components/ui/MiddleEllipsis/TruncateTextCharacterMap.js
@@ -0,0 +1,100 @@
+export default {
+    "inter": {
+        "0": 10.062,
+        "1": 6.428,
+        "2": 9.671,
+        "3": 9.848,
+        "4": 10.285,
+        "5": 9.462,
+        "6": 9.857,
+        "7": 9.121,
+        "8": 9.833,
+        "9": 9.857,
+        " ": 4.444,
+        "!": 4.480,
+        "\"": 7.342,
+        "#": 10.072,
+        "$": 10.217,
+        "%": 15.465,
+        "&": 10.241,
+        "'": 4.715,
+        "(": 5.718,
+        ")": 5.718,
+        "*": 7.958,
+        "+": 10.526,
+        ",": 4.487,
+        "-": 7.303,
+        ".": 4.487,
+        "/": 5.703,
+        ":": 4.487,
+        ";": 4.687,
+        "<": 10.526,
+        "=": 10.526,
+        ">": 10.526,
+        "?": 8.202,
+        "@": 15.467,
+        "A": 11.086,
+        "B": 10.440,
+        "C": 11.672,
+        "D": 11.489,
+        "E": 9.578,
+        "F": 9.381,
+        "G": 11.909,
+        "H": 11.828,
+        "I": 4.232,
+        "J": 9.068,
+        "K": 10.683,
+        "L": 8.993,
+        "M": 14.371,
+        "N": 11.977,
+        "O": 12.206,
+        "P": 10.171,
+        "Q": 12.206,
+        "R": 10.276,
+        "S": 10.217,
+        "T": 10.265,
+        "U": 11.833,
+        "V": 11.099,
+        "W": 15.888,
+        "X": 10.848,
+        "Y": 10.795,
+        "Z": 10.034,
+        "[": 5.718,
+        "\\": 5.316,
+        "]": 5.718,
+        "^": 7.479,
+        "_": 7.293,
+        "`": 5.019,
+        "a": 8.906,
+        "b": 9.713,
+        "c": 9.054,
+        "d": 9.713,
+        "e": 9.244,
+        "f": 5.504,
+        "g": 9.727,
+        "h": 9.381,
+        "i": 3.810,
+        "j": 3.810,
+        "k": 8.707,
+        "l": 3.810,
+        "m": 13.949,
+        "n": 9.375,
+        "o": 9.503,
+        "p": 9.713,
+        "q": 9.713,
+        "r": 6.038,
+        "s": 8.350,
+        "t": 5.175,
+        "u": 9.381,
+        "v": 8.902,
+        "w": 12.975,
+        "x": 8.664,
+        "y": 8.902,
+        "z": 8.704,
+        "{": 6.746,
+        "|": 5.255,
+        "}": 6.746,
+        "~": 10.526,
+        "": 0
+    }
+}
diff --git a/resources/js/components/ui/index.js b/resources/js/components/ui/index.js
index aa0127f5660..4f4909880e3 100644
--- a/resources/js/components/ui/index.js
+++ b/resources/js/components/ui/index.js
@@ -47,6 +47,7 @@ export { default as InputGroup } from './Input/Group.vue';
 export { default as InputGroupAppend } from './Input/GroupAppend.vue';
 export { default as InputGroupPrepend } from './Input/GroupPrepend.vue';
 export { default as Label } from './Label.vue';
+export { default as MiddleEllipsis } from './MiddleEllipsis/MiddleEllipsis.vue';
 export { default as Modal } from './Modal/Modal.vue';
 export { default as ModalClose } from './Modal/Close.vue';
 export { default as ModalTitle } from './Modal/Title.vue';
diff --git a/resources/js/tests/Package.test.js b/resources/js/tests/Package.test.js
index b7ead20e94b..5d43ccfb22c 100644
--- a/resources/js/tests/Package.test.js
+++ b/resources/js/tests/Package.test.js
@@ -167,6 +167,7 @@ it('exports ui', async () => {
         'InputGroupAppend',
         'InputGroupPrepend',
         'Label',
+        'MiddleEllipsis',
         'Modal',
         'ModalClose',
         'ModalTitle',