diff --git a/src/utils/file_upload.rs b/src/utils/file_upload.rs
index 7a53adac0c..fbcaca92c9 100644
--- a/src/utils/file_upload.rs
+++ b/src/utils/file_upload.rs
@@ -300,7 +300,7 @@ fn upload_files_chunked(
     ));
 
     upload_chunks(&chunks, options, progress_style)?;
-    println!("{} Uploaded release files to Sentry", style(">").dim(),);
+    println!("{} Uploaded release files to Sentry", style(">").dim());
 
     let progress_style = ProgressStyle::default_spinner().template("{spinner} Processing files...");
 
@@ -443,6 +443,8 @@ fn build_artifact_bundle(context: &UploadContext, files: &SourceFiles) -> Result
 
     bundle.finish()?;
 
+    pb.finish_with_duration("Bundling");
+
     println!(
         "{} Bundled {} {} for upload",
         style(">").dim(),
@@ -453,8 +455,6 @@ fn build_artifact_bundle(context: &UploadContext, files: &SourceFiles) -> Result
         }
     );
 
-    pb.finish_with_duration("Bundling");
-
     Ok(archive)
 }
 
diff --git a/src/utils/sourcemaps.rs b/src/utils/sourcemaps.rs
index 18152be543..58774b6546 100644
--- a/src/utils/sourcemaps.rs
+++ b/src/utils/sourcemaps.rs
@@ -591,14 +591,18 @@ impl SourceMapProcessor {
         Ok(())
     }
 
-    fn flag_uploaded_sources(&mut self, context: &UploadContext<'_>) {
+    /// Flags the collected sources whether they have already been uploaded before
+    /// (based on their checksum), and returns the number of files that *do* need an upload.
+    fn flag_uploaded_sources(&mut self, context: &UploadContext<'_>) -> usize {
+        let mut files_needing_upload = self.sources.len();
+
         // TODO: this endpoint does not exist for non release based uploads
         if !context.dedupe {
-            return;
+            return files_needing_upload;
         }
         let release = match context.release {
             Some(release) => release,
-            None => return,
+            None => return files_needing_upload,
         };
 
         let mut sources_checksums: Vec<_> = self
@@ -618,8 +622,8 @@ impl SourceMapProcessor {
             release,
             &sources_checksums,
         ) {
-            let already_uploaded_checksums: Vec<_> = artifacts
-                .iter()
+            let already_uploaded_checksums: HashSet<_> = artifacts
+                .into_iter()
                 .filter_map(|artifact| Digest::from_str(&artifact.sha1).ok())
                 .collect();
 
@@ -627,21 +631,27 @@ impl SourceMapProcessor {
                 if let Ok(checksum) = source.checksum() {
                     if already_uploaded_checksums.contains(&checksum) {
                         source.already_uploaded = true;
+                        files_needing_upload -= 1;
                     }
                 }
             }
         }
+        files_needing_upload
     }
 
     /// Uploads all files
     pub fn upload(&mut self, context: &UploadContext<'_>) -> Result<()> {
         initialize_legacy_release_upload(context)?;
         self.flush_pending_sources();
-        self.flag_uploaded_sources(context);
-        let mut uploader = FileUpload::new(context);
-        uploader.files(&self.sources);
-        uploader.upload()?;
-        self.dump_log("Source Map Upload Report");
+        let files_needing_upload = self.flag_uploaded_sources(context);
+        if files_needing_upload > 0 {
+            let mut uploader = FileUpload::new(context);
+            uploader.files(&self.sources);
+            uploader.upload()?;
+            self.dump_log("Source Map Upload Report");
+        } else {
+            println!("{} Nothing to upload", style(">").dim());
+        }
         Ok(())
     }
 
diff --git a/tests/integration/_cases/releases/releases-files-upload-sourcemaps.trycmd b/tests/integration/_cases/releases/releases-files-upload-sourcemaps.trycmd
index 399f64591f..f66da7a86f 100644
--- a/tests/integration/_cases/releases/releases-files-upload-sourcemaps.trycmd
+++ b/tests/integration/_cases/releases/releases-files-upload-sourcemaps.trycmd
@@ -3,15 +3,6 @@ $ sentry-cli releases files wat-release upload-sourcemaps --url-prefix '~/assets
 ? success
 > Rewriting sources
 > Adding source map references
-> Bundled 0 files for upload
-> Uploaded release files to Sentry
-> File upload complete (processing pending on server)
-> Organization: wat-org
-> Project: wat-project
-> Release: wat-release
-> Dist: None
-> Upload type: release bundle
-
-Source Map Upload Report
+> Nothing to upload
 
 ```
diff --git a/tests/integration/sourcemaps/upload.rs b/tests/integration/sourcemaps/upload.rs
index 332ac9ac6f..f5f006b437 100644
--- a/tests/integration/sourcemaps/upload.rs
+++ b/tests/integration/sourcemaps/upload.rs
@@ -146,8 +146,8 @@ fn command_sourcemaps_upload_modern() {
 }
 
 #[test]
-fn command_releases_files_upload_sourcemap() {
-    let upload_endpoints = mock_common_upload_endpoints(ServerBehavior::Legacy);
+fn command_sourcemaps_upload_empty() {
+    let _upload_endpoints = mock_common_upload_endpoints(ServerBehavior::Legacy);
     let _files = mock_endpoint(
         EndpointOptions::new(
             "GET",
@@ -157,5 +157,4 @@ fn command_releases_files_upload_sourcemap() {
         .with_response_body("[]"),
     );
     register_test("releases/releases-files-upload-sourcemaps.trycmd");
-    assert_endpoints(&upload_endpoints);
 }