diff --git a/src/PowderCoating.Web/wwwroot/js/item-wizard.js b/src/PowderCoating.Web/wwwroot/js/item-wizard.js
index 333ebb6..eb2a6cc 100644
--- a/src/PowderCoating.Web/wwwroot/js/item-wizard.js
+++ b/src/PowderCoating.Web/wwwroot/js/item-wizard.js
@@ -1166,16 +1166,50 @@ function aiHandleDrop(event) {
     Array.from(event.dataTransfer.files).forEach(aiUploadFile);
 }
 
+// Resize + recompress an image file before upload so phone photos (5-15 MB)
+// don't saturate mobile upload bandwidth or slow down Anthropic processing.
+// Max 1200px on the long edge, JPEG at 85% quality — ~150-250 KB typical output.
+// Non-image files and GIFs are returned unchanged.
+async function aiCompressImage(file, maxPx = 1200, quality = 0.85) {
+    if (!file.type.startsWith('image/') || file.type === 'image/gif') return file;
+    return new Promise(resolve => {
+        const reader = new FileReader();
+        reader.onload = e => {
+            const img = new Image();
+            img.onload = () => {
+                const scale = Math.min(1, maxPx / Math.max(img.width, img.height));
+                const w = Math.round(img.width * scale);
+                const h = Math.round(img.height * scale);
+                const canvas = document.createElement('canvas');
+                canvas.width  = w;
+                canvas.height = h;
+                canvas.getContext('2d').drawImage(img, 0, 0, w, h);
+                canvas.toBlob(blob => {
+                    if (!blob || blob.size >= file.size) { resolve(file); return; }
+                    resolve(new File([blob], file.name.replace(/\.[^.]+$/, '.jpg'), { type: 'image/jpeg' }));
+                }, 'image/jpeg', quality);
+            };
+            img.onerror = () => resolve(file);
+            img.src = e.target.result;
+        };
+        reader.onerror = () => resolve(file);
+        reader.readAsDataURL(file);
+    });
+}
+
 async function aiUploadFile(file) {
-    // Read as data: URL — blob: URLs are blocked by CSP; data: is explicitly allowed
+    // Compress before uploading — full-res phone photos slow upload + Anthropic API
+    const compressed = await aiCompressImage(file);
+
+    // Read compressed bytes for the thumbnail preview (blob: URLs blocked by CSP)
     const previewUrl = await new Promise(resolve => {
         const reader = new FileReader();
         reader.onload = e => resolve(e.target.result);
         reader.onerror = () => resolve('');
-        reader.readAsDataURL(file);
+        reader.readAsDataURL(compressed);
     });
     const formData = new FormData();
-    formData.append('file', file);
+    formData.append('file', compressed);
     formData.append('__RequestVerificationToken',
         document.querySelector('input[name="__RequestVerificationToken"]')?.value || '');
 
@@ -1278,15 +1312,27 @@ async function aiAnalyze() {
     };
 
     const analyzeUrl = pageMeta.aiAnalyzeUrl || '/Quotes/AiAnalyzeItem';
+    const controller = new AbortController();
+    // Abort after 120 s — server-side Anthropic timeout is 60 s per attempt with retries;
+    // 120 s gives room for one retry plus network round-trip on a slow mobile connection.
+    const hardTimeout   = setTimeout(() => controller.abort(), 120_000);
+    // After 30 s without a response, update the spinner text so the user knows it's working.
+    const slowWarning   = setTimeout(() => {
+        const t = document.getElementById('ai_loadingText');
+        if (t) t.textContent = 'Still analyzing… this can take a minute on mobile connections.';
+    }, 30_000);
     try {
         const resp = await fetch(analyzeUrl, {
             method: 'POST',
+            signal: controller.signal,
             headers: {
                 'Content-Type': 'application/json',
                 'RequestVerificationToken': document.querySelector('input[name="__RequestVerificationToken"]')?.value || ''
             },
             body: JSON.stringify(payload)
         });
+        clearTimeout(hardTimeout);
+        clearTimeout(slowWarning);
         if (!resp.ok) {
             if (resp.status === 401 || resp.status === 302 || resp.redirected) {
                 throw new Error('Your session has expired. Please refresh the page and sign in again.');
@@ -1301,9 +1347,15 @@ async function aiAnalyze() {
         const result = await resp.json();
         aiHandleResult(result);
     } catch (err) {
+        clearTimeout(hardTimeout);
+        clearTimeout(slowWarning);
         console.error('AI analyze error:', err);
         aiSetLoading(false);
-        aiShowError(err.message);
+        if (err.name === 'AbortError') {
+            aiShowError('The request timed out — your connection may be slow. Please try again.');
+        } else {
+            aiShowError(err.message);
+        }
     }
 }
 
@@ -1340,15 +1392,24 @@ async function aiSendFollowup() {
     };
 
     const analyzeUrl = pageMeta.aiAnalyzeUrl || '/Quotes/AiAnalyzeItem';
+    const controller2  = new AbortController();
+    const hardTimeout2 = setTimeout(() => controller2.abort(), 120_000);
+    const slowWarning2 = setTimeout(() => {
+        const t = document.getElementById('ai_loadingText');
+        if (t) t.textContent = 'Still analyzing… this can take a minute on mobile connections.';
+    }, 30_000);
     try {
         const resp = await fetch(analyzeUrl, {
             method: 'POST',
+            signal: controller2.signal,
             headers: {
                 'Content-Type': 'application/json',
                 'RequestVerificationToken': document.querySelector('input[name="__RequestVerificationToken"]')?.value || ''
             },
             body: JSON.stringify(payload)
         });
+        clearTimeout(hardTimeout2);
+        clearTimeout(slowWarning2);
         if (!resp.ok) {
             if (resp.status === 401 || resp.status === 302 || resp.redirected) {
                 throw new Error('Your session has expired. Please refresh the page and sign in again.');
@@ -1362,9 +1423,15 @@ async function aiSendFollowup() {
         const result = await resp.json();
         aiHandleResult(result);
     } catch (err) {
+        clearTimeout(hardTimeout2);
+        clearTimeout(slowWarning2);
         console.error('AI follow-up error:', err);
         aiSetLoading(false);
-        aiShowError(err.message);
+        if (err.name === 'AbortError') {
+            aiShowError('The request timed out — your connection may be slow. Please try again.');
+        } else {
+            aiShowError(err.message);
+        }
     }
 }
 
@@ -1445,12 +1512,14 @@ function aiRemoveTag(tag) {
 }
 
 function aiSetLoading(isLoading) {
-    const btn = document.getElementById('ai_analyzeBtn');
+    const btn     = document.getElementById('ai_analyzeBtn');
     const spinner = document.getElementById('ai_loadingSpinner');
-    const text = document.getElementById('ai_loadingText');
+    const text    = document.getElementById('ai_loadingText');
     if (btn) btn.disabled = isLoading;
     spinner?.classList.toggle('d-none', !isLoading);
     text?.classList.toggle('d-none', !isLoading);
+    // Reset text so a retry after the slow-connection warning shows the default message
+    if (!isLoading && text) text.textContent = 'Analyzing photos, please wait…';
 }
 
 function aiShowError(message) {