diff --git a/CHANGELOG.md b/CHANGELOG.md
index 83bbc211..3bdf2956 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -13,7 +13,8 @@ Any BREAKING CHANGE between minor versions will be documented here in upper case
 
 ### Fixed
 
-- `Site.copy` now works as expected when given a path with a trailing slash. [#426]
+- `Site.copy` now supports trailing slashes in the source path. [#426]
+- Multiple `Site.copy` calls can now be used to copy one file to multiple destinations. [#429]
 
 ## [1.17.4] - 2023-05-25
 ### Added
@@ -2261,6 +2262,7 @@ The first version.
 [#418]: https://github.com/lumeland/lume/issues/418
 [#419]: https://github.com/lumeland/lume/issues/419
 [#426]: https://github.com/lumeland/lume/pull/426
+[#429]: https://github.com/lumeland/lume/pull/429
 
 [1.17.4]: https://github.com/lumeland/lume/compare/v1.17.3...v1.17.4
 [1.17.3]: https://github.com/lumeland/lume/compare/v1.17.2...v1.17.3
diff --git a/core/fs.ts b/core/fs.ts
index 4e5a5103..7df126cd 100644
--- a/core/fs.ts
+++ b/core/fs.ts
@@ -12,11 +12,17 @@ export interface Options {
 export type Loader = (path: string) => Promise<Data>;
 
 export class Entry {
+  /** The name of the file/dir. */
   name: string;
+  /** The normalized path of the file/dir. */
   path: string;
+  /** The type of the entry. */
   type: EntryType;
+  /** The absolute file path. */
   src: string;
+  /** The children of the entry. */
   children = new Map<string, Entry>();
+  /** Temporary flags that are cleared when a file is modified. */
   flags = new Set<string>();
   #content = new Map<Loader, Promise<Data> | Data>();
   #info?: Deno.FileInfo;
diff --git a/core/source.ts b/core/source.ts
index 864e615d..9b0597e3 100644
--- a/core/source.ts
+++ b/core/source.ts
@@ -58,10 +58,11 @@ export default class Source {
   prettyUrls: boolean;
 
   /** List of static files and folders to copy */
-  staticPaths = new Map<
-    string,
-    { dest: string | ((path: string) => string) | undefined; dirOnly: boolean }
-  >();
+  staticPaths: {
+    from: string;
+    to: string | ((path: string) => string) | undefined;
+    dirOnly: boolean;
+  }[] = [];
 
   /** List of static files and folders to copy */
   copyRemainingFiles?: (path: string) => string | boolean;
@@ -102,10 +103,10 @@ export default class Source {
   }
 
   addStaticPath(from: string, to?: string | ((path: string) => string)) {
-    this.staticPaths.set(
-      normalizePath(from.replace(/\/$/, "")),
+    this.staticPaths.push(
       {
-        dest: typeof to === "string" ? normalizePath(to) : to,
+        from: normalizePath(from.replace(/\/$/, "")),
+        to: typeof to === "string" ? normalizePath(to) : to,
         dirOnly: from.endsWith("/"),
       },
     );
@@ -118,12 +119,42 @@ export default class Source {
     const pages: Page[] = [];
     const staticFiles: StaticFile[] = [];
 
+    // Resolve staticPaths to staticFiles
+    for (const instruction of this.staticPaths) {
+      const entry = this.fs.entries.get(instruction.from);
+      if (entry) {
+        const path = posix.dirname(entry.path);
+
+        if (entry.type == "file") {
+          if (instruction.dirOnly) {
+            continue;
+          }
+          staticFiles.push({
+            entry,
+            outputPath: getOutputPath(
+              entry,
+              path,
+              instruction.to,
+            ),
+          });
+        } else {
+          const dest = instruction.to;
+          staticFiles.push(...this.#getStaticFiles(
+            entry,
+            typeof dest === "string" ? dest : posix.join(path, entry.name),
+            typeof dest === "function" ? dest : undefined,
+          ));
+        }
+      }
+    }
+
     await this.#build(
       buildFilters,
       this.fs.entries.get("/")!,
       "/",
       globalComponents,
       {},
+      new Set(this.staticPaths.map((p) => p.from)),
       pages,
       staticFiles,
     );
@@ -140,6 +171,7 @@ export default class Source {
     path: string,
     parentComponents: Components,
     parentData: Data,
+    staticPaths: Set<string>,
     pages: Page[],
     staticFiles: StaticFile[],
   ) {
@@ -191,26 +223,8 @@ export default class Source {
         continue;
       }
 
-      // Static files
-      if (this.staticPaths.has(entry.path)) {
-        const { dest, dirOnly } = this.staticPaths.get(entry.path)!;
-
-        if (entry.type === "file") {
-          if (dirOnly) {
-            continue;
-          }
-          staticFiles.push({
-            entry,
-            outputPath: getOutputPath(entry, path, dest),
-          });
-          continue;
-        }
-
-        staticFiles.push(...this.#getStaticFiles(
-          entry,
-          typeof dest === "string" ? dest : posix.join(path, entry.name),
-          typeof dest === "function" ? dest : undefined,
-        ));
+      if (staticPaths.has(entry.path)) {
+        // The static file has already been resolved.
         continue;
       }
 
@@ -311,6 +325,7 @@ export default class Source {
           path,
           parentComponents,
           dirData,
+          staticPaths,
           pages,
           staticFiles,
         );
@@ -691,13 +706,18 @@ export function getOutputPath(
   path: string,
   dest?: string | ((path: string) => string),
 ): string {
-  if (typeof dest === "function") {
-    return dest(posix.join(path, entry.name));
-  }
-
   if (typeof dest === "string") {
     return dest;
   }
 
-  return posix.join(path, entry.name);
+  const outputPath = posix.join(
+    path.split("/").map((comp) => parseDate(comp)[0]).join("/"),
+    entry.name,
+  );
+
+  if (typeof dest === "function") {
+    return dest(outputPath);
+  }
+
+  return outputPath;
 }
diff --git a/core/writer.ts b/core/writer.ts
index 081f6b3e..7e336cdc 100644
--- a/core/writer.ts
+++ b/core/writer.ts
@@ -112,6 +112,7 @@ export default class Writer {
 
   /**
    * Copy the static files in the dest folder
+   * Returns the static files that have been successfully copied
    */
   async copyFiles(files: StaticFile[]): Promise<StaticFile[]> {
     const copyFiles: StaticFile[] = [];
@@ -135,11 +136,11 @@ export default class Writer {
   async copyFile(file: StaticFile): Promise<boolean> {
     const { entry } = file;
 
-    if (entry.flags.has("saved")) {
+    if (entry.flags.has("saved-" + file.outputPath)) {
       return false;
     }
 
-    entry.flags.add("saved");
+    entry.flags.add("saved-" + file.outputPath);
 
     const pathTo = posix.join(this.dest, file.outputPath);
 
diff --git a/tests/__snapshots__/static_files.test.ts.snap b/tests/__snapshots__/static_files.test.ts.snap
index 19db3953..2b9cb23a 100644
--- a/tests/__snapshots__/static_files.test.ts.snap
+++ b/tests/__snapshots__/static_files.test.ts.snap
@@ -91,6 +91,16 @@ snapshot[`Copy static files 2`] = `
     flags: [],
     outputPath: "/_headers",
   },
+  {
+    entry: "/one.yes",
+    flags: [],
+    outputPath: "/one.yes",
+  },
+  {
+    entry: "/one.yes",
+    flags: [],
+    outputPath: "/one-again.yes",
+  },
   {
     entry: "/other/one",
     flags: [],
@@ -166,6 +176,11 @@ snapshot[`Copy static files 2`] = `
     flags: [],
     outputPath: "/script/app/main.js",
   },
+  {
+    entry: "/static/_redirects",
+    flags: [],
+    outputPath: "/_redirects",
+  },
   {
     entry: "/static/one.yes",
     flags: [],
diff --git a/tests/config.test.ts b/tests/config.test.ts
index f9600c79..5b7fce04 100644
--- a/tests/config.test.ts
+++ b/tests/config.test.ts
@@ -23,20 +23,19 @@ Deno.test("static files configuration", () => {
   const { staticPaths } = site.source;
 
   site.copy("img");
-  equals(staticPaths.size, 1);
-  equals(staticPaths.has("/img"), true);
-  equals(staticPaths.get("/img")!.dest, undefined);
+  equals(staticPaths.length, 1);
+  equals(staticPaths[0].from, "/img");
+  equals(staticPaths[0].to, undefined);
 
   site.copy("statics/favicon.ico", "favicon.ico");
-  equals(staticPaths.size, 2);
-  equals(
-    staticPaths.get("/statics/favicon.ico")!.dest,
-    "/favicon.ico",
-  );
+  equals(staticPaths.length, 2);
+  equals(staticPaths[1].from, "/statics/favicon.ico");
+  equals(staticPaths[1].to, "/favicon.ico");
 
   site.copy("css", ".");
-  equals(staticPaths.size, 3);
-  equals(staticPaths.get("/css")!.dest, "/");
+  equals(staticPaths.length, 3);
+  equals(staticPaths[2].from, "/css");
+  equals(staticPaths[2].to, "/");
 });
 
 Deno.test("ignored files configuration", () => {
diff --git a/tests/static_files.test.ts b/tests/static_files.test.ts
index cebec113..edbbd637 100644
--- a/tests/static_files.test.ts
+++ b/tests/static_files.test.ts
@@ -21,6 +21,10 @@ Deno.test("Copy static files", async (t) => {
     (file) => "/subdir" + file.replace(/\.copy2/, ".copy3"),
   );
 
+  // a single file can be copied multiple times
+  site.copy("one.yes");
+  site.copy("one.yes", "one-again.yes");
+
   // copied with the trailing slash
   site.copy("other2/");