diff --git a/src/components/cases/collections-tab.tsx b/src/components/cases/collections-tab.tsx
index bb93ed6..0cf5247 100644
--- a/src/components/cases/collections-tab.tsx
+++ b/src/components/cases/collections-tab.tsx
@@ -31,6 +31,7 @@ import {
 import { supabase } from "@/integrations/supabase/client";
 import { useAuth } from "@/lib/auth";
 import { formatCurrency, formatDate } from "@/lib/format";
+import { promptFilename } from "@/lib/prompt-filename";
 import {
   ArrowLeft,
   Calculator,
@@ -544,9 +545,11 @@ export function CollectionDetail({
       ].join(",")),
     ].join("\n");
     const blob = new Blob([rows], { type: "text/csv" });
+    const name = promptFilename(`Statement_${ho?.last_name || "homeowner"}`, "csv");
+    if (!name) return;
     const a = document.createElement("a");
     a.href = URL.createObjectURL(blob);
-    a.download = `Statement_${ho?.last_name || "homeowner"}.csv`;
+    a.download = `${name}.csv`;
     a.click();
   };
 
diff --git a/src/components/forms/custom-form-builder.tsx b/src/components/forms/custom-form-builder.tsx
index 54e7e68..e53229a 100644
--- a/src/components/forms/custom-form-builder.tsx
+++ b/src/components/forms/custom-form-builder.tsx
@@ -91,6 +91,7 @@ import {
 } from "docx";
 import { toast } from "sonner";
 import { supabase } from "@/integrations/supabase/client";
+import { promptFilename } from "@/lib/prompt-filename";
 
 // Paragraph extension with indent (px) + caption flag, persisted as inline styles
 const PaddedParagraph = Paragraph.extend({
@@ -1026,19 +1027,21 @@ export function CustomFormBuilder() {
       y += seg.caption ? 2 : 4;
     }
 
-    const filenameBase = (renderTitle(ctx) || "Custom_Form").replace(/\s+/g, "_");
+    const defaultName = (renderTitle(ctx) || "Custom_Form").replace(/\s+/g, "_");
     if (saveToCase && selectedCaseId) {
       const blob = doc.output("blob");
       await savePdfToDocuments({
         blob,
         caseId: selectedCaseId,
-        name: `${filenameBase}.pdf`,
+        name: `${defaultName}.pdf`,
         mimeType: "application/pdf",
       });
       toast.success("Saved to case files");
       setSaveToCaseOpen(false);
     } else {
-      doc.save(`${filenameBase}.pdf`);
+      const name = promptFilename(defaultName, "pdf");
+      if (!name) return;
+      doc.save(`${name}.pdf`);
       toast.success("PDF downloaded");
     }
   };
@@ -1236,22 +1239,24 @@ export function CustomFormBuilder() {
     });
 
     const blob = await Packer.toBlob(docx);
-    const filenameBase = (renderTitle(ctx) || "Custom_Form").replace(/\s+/g, "_");
+    const defaultName = (renderTitle(ctx) || "Custom_Form").replace(/\s+/g, "_");
 
     if (saveToCase && selectedCaseId) {
       await savePdfToDocuments({
         blob,
         caseId: selectedCaseId,
-        name: `${filenameBase}.docx`,
+        name: `${defaultName}.docx`,
         mimeType: "application/vnd.openxmlformats-officedocument.wordprocessingml.document",
       });
       toast.success("Saved to case files");
       setSaveToCaseOpen(false);
     } else {
+      const name = promptFilename(defaultName, "docx");
+      if (!name) return;
       const url = URL.createObjectURL(blob);
       const a = document.createElement("a");
       a.href = url;
-      a.download = `${filenameBase}.docx`;
+      a.download = `${name}.docx`;
       a.click();
       URL.revokeObjectURL(url);
       toast.success("DOCX downloaded");
diff --git a/src/components/forms/estoppel-form.tsx b/src/components/forms/estoppel-form.tsx
index a2c7d62..51c5b16 100644
--- a/src/components/forms/estoppel-form.tsx
+++ b/src/components/forms/estoppel-form.tsx
@@ -15,6 +15,7 @@ import {
   type FirmInfo,
 } from "@/lib/forms-shared";
 import { fillTokens, loadFormTemplate, type FormTemplateConfig } from "@/lib/form-templates";
+import { promptFilename } from "@/lib/prompt-filename";
 import { jsPDF } from "jspdf";
 import { toast } from "sonner";
 
@@ -266,7 +267,9 @@ export function EstoppelForm() {
       doc.text(al, margin, y);
     }
 
-    doc.save(`Estoppel_${parcelId || "draft"}_${date}.pdf`);
+    const name = promptFilename(`Estoppel_${parcelId || "draft"}_${date}`, "pdf");
+    if (!name) return;
+    doc.save(`${name}.pdf`);
     toast.success("Estoppel PDF downloaded");
   };
 
diff --git a/src/components/forms/itf-form.tsx b/src/components/forms/itf-form.tsx
index 47e2a24..21f6c22 100644
--- a/src/components/forms/itf-form.tsx
+++ b/src/components/forms/itf-form.tsx
@@ -16,6 +16,7 @@ import {
   type FirmInfo,
 } from "@/lib/forms-shared";
 import { buildLetterTokens, loadFormTemplate, renderLetterPdf, type FormTemplateConfig } from "@/lib/form-templates";
+import { promptFilename } from "@/lib/prompt-filename";
 import { toast } from "sonner";
 
 export function ItfForm() {
@@ -106,7 +107,9 @@ export function ItfForm() {
       filename: `ITF_${ownerFullName(homeowner) || "draft"}_${letterDate}`,
     });
 
-    doc.save(`ITF_${ownerFullName(homeowner) || "draft"}_${letterDate}.pdf`);
+    const name = promptFilename(`ITF_${ownerFullName(homeowner) || "draft"}_${letterDate}`, "pdf");
+    if (!name) return;
+    doc.save(`${name}.pdf`);
     toast.success("ITF PDF downloaded");
   };
 
diff --git a/src/components/forms/itl-form.tsx b/src/components/forms/itl-form.tsx
index 74dedd9..15722fc 100644
--- a/src/components/forms/itl-form.tsx
+++ b/src/components/forms/itl-form.tsx
@@ -16,6 +16,7 @@ import {
   type FirmInfo,
 } from "@/lib/forms-shared";
 import { buildLetterTokens, loadFormTemplate, renderLetterPdf, type FormTemplateConfig } from "@/lib/form-templates";
+import { promptFilename } from "@/lib/prompt-filename";
 import { toast } from "sonner";
 
 export function ItlForm() {
@@ -95,7 +96,9 @@ export function ItlForm() {
       filename: `ITL_${ownerFullName(homeowner) || "draft"}_${letterDate}`,
     });
 
-    doc.save(`ITL_${ownerFullName(homeowner) || "draft"}_${letterDate}.pdf`);
+    const name = promptFilename(`ITL_${ownerFullName(homeowner) || "draft"}_${letterDate}`, "pdf");
+    if (!name) return;
+    doc.save(`${name}.pdf`);
     toast.success("ITL PDF downloaded");
   };
 
diff --git a/src/components/forms/letter-generator.tsx b/src/components/forms/letter-generator.tsx
index 8342947..c16e289 100644
--- a/src/components/forms/letter-generator.tsx
+++ b/src/components/forms/letter-generator.tsx
@@ -17,6 +17,7 @@ import {
   type FirmInfo,
 } from "@/lib/forms-shared";
 import { fillTokens, loadFormTemplate, type FormTemplateConfig } from "@/lib/form-templates";
+import { promptFilename } from "@/lib/prompt-filename";
 import { supabase } from "@/integrations/supabase/client";
 import { jsPDF } from "jspdf";
 import { toast } from "sonner";
@@ -290,7 +291,9 @@ export function LetterGenerator() {
       }
     }
 
-    doc.save(`Letter_${date}.pdf`);
+    const name = promptFilename(`Letter_${date}`, "pdf");
+    if (!name) return;
+    doc.save(`${name}.pdf`);
     toast.success("Letter PDF downloaded");
   };
 
diff --git a/src/components/forms/nola-form.tsx b/src/components/forms/nola-form.tsx
index 7f1ca25..a5d4f29 100644
--- a/src/components/forms/nola-form.tsx
+++ b/src/components/forms/nola-form.tsx
@@ -15,6 +15,7 @@ import {
   type FirmInfo,
 } from "@/lib/forms-shared";
 import { buildLetterTokens, loadFormTemplate, renderLetterPdf, type FormTemplateConfig } from "@/lib/form-templates";
+import { promptFilename } from "@/lib/prompt-filename";
 import { toast } from "sonner";
 
 interface Item {
@@ -94,7 +95,9 @@ export function NolaForm() {
       filename: `NOLA_${ownerFullName(homeowner) || "draft"}_${date}`,
     });
 
-    doc.save(`NOLA_${ownerFullName(homeowner) || "draft"}_${date}.pdf`);
+    const name = promptFilename(`NOLA_${ownerFullName(homeowner) || "draft"}_${date}`, "pdf");
+    if (!name) return;
+    doc.save(`${name}.pdf`);
     toast.success("NOLA PDF downloaded");
   };
 
diff --git a/src/lib/prompt-filename.ts b/src/lib/prompt-filename.ts
new file mode 100644
index 0000000..5dcaee2
--- /dev/null
+++ b/src/lib/prompt-filename.ts
@@ -0,0 +1,17 @@
+/**
+ * Prompts the user for a filename before download. Returns the chosen base
+ * name (without extension) sanitized for filesystem use, or null if cancelled.
+ *
+ * @param defaultName Suggested base name (no extension)
+ * @param ext Extension shown to the user, e.g. "pdf", "docx", "csv"
+ */
+export function promptFilename(defaultName: string, ext: string): string | null {
+  const sanitize = (s: string) => s.replace(/[\\/:*?"<>|]+/g, "_").trim();
+  const cleanDefault = sanitize(defaultName).replace(new RegExp(`\\.${ext}$`, "i"), "") || "Document";
+  const input = typeof window !== "undefined"
+    ? window.prompt(`File name (.${ext})`, cleanDefault)
+    : cleanDefault;
+  if (input === null) return null; // user cancelled
+  const cleaned = sanitize(input).replace(new RegExp(`\\.${ext}$`, "i"), "");
+  return cleaned || cleanDefault;
+}
diff --git a/src/routes/documents.pleading.new.tsx b/src/routes/documents.pleading.new.tsx
index 42998ac..897c953 100644
--- a/src/routes/documents.pleading.new.tsx
+++ b/src/routes/documents.pleading.new.tsx
@@ -22,6 +22,7 @@ import { useAuth } from "@/lib/auth";
 import { toast } from "sonner";
 import { Download, FileText, Save, Loader2, Plus, Trash2, PenLine, Users, Variable, Copy } from "lucide-react";
 import { applyVars, buildChips, buildVarMap, loadPleadingContext, type LoadedContext, type VarChip } from "@/lib/pleading-variables";
+import { promptFilename } from "@/lib/prompt-filename";
 import { Badge } from "@/components/ui/badge";
 
 export const Route = createFileRoute("/documents/pleading/new")({
@@ -244,11 +245,15 @@ function PleadingNewPage() {
   const headerLine2 = `IN AND FOR ${county.toUpperCase()} COUNTY, FLORIDA`;
 
   const onDownload = async () => {
-    await downloadPleading(input, docName || "Pleading");
+    const name = promptFilename(docName || "Pleading", "docx");
+    if (!name) return;
+    await downloadPleading(input, name);
   };
 
   const onDownloadPdf = async () => {
-    await downloadPleadingPdf(input, docName || "Pleading");
+    const name = promptFilename(docName || "Pleading", "pdf");
+    if (!name) return;
+    await downloadPleadingPdf(input, name);
   };
 
   const onSave = async () => {
diff --git a/src/routes/documents.templates.$templateId.tsx b/src/routes/documents.templates.$templateId.tsx
index 0e324bd..e48b60c 100644
--- a/src/routes/documents.templates.$templateId.tsx
+++ b/src/routes/documents.templates.$templateId.tsx
@@ -12,6 +12,7 @@ import { useAuth } from "@/lib/auth";
 import { toast } from "sonner";
 import { Download, Loader2, Save, Trash2 } from "lucide-react";
 import { downloadGeneric } from "@/lib/docx-pleading";
+import { promptFilename } from "@/lib/prompt-filename";
 import { Packer } from "docx";
 
 export const Route = createFileRoute("/documents/templates/$templateId")({
@@ -120,9 +121,11 @@ function TemplateDetailPage() {
   const fontSizePt: number = tpl?.font_size_pt || 12;
 
   const downloadOnly = async () => {
+    const name = promptFilename(docName || "Document", "docx");
+    if (!name) return;
     await downloadGeneric(
       { title: isLetter ? undefined : docName, body: merged, fontFamily, fontSizePt },
-      docName || "Document",
+      name,
     );
   };