diff --git a/Changelog.md b/Changelog.md
index e5235224b..911afec41 100644
--- a/Changelog.md
+++ b/Changelog.md
@@ -10,6 +10,7 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
  * Change manylinux default version based on target arch by messense in [#424](https://github.com/PyO3/maturin/pull/424)
  * Support local path dependencies in source distribution (i.e. you can now package a workspace into an sdist)
  * Set a more reasonable LC_ID_DYLIB entry on macOS by messense [#433](https://github.com/PyO3/maturin/pull/433)
+ * Add `--skip-existing` option to publish by messense [#444](https://github.com/PyO3/maturin/pull/444)
 
 ## 0.9.4 - 2021-02-18
 
diff --git a/Readme.md b/Readme.md
index 10d5fb07c..91e021faa 100644
--- a/Readme.md
+++ b/Readme.md
@@ -277,6 +277,10 @@ FLAGS:
         --skip-auditwheel
             Don't check for manylinux compliance
 
+        --skip-existing
+            Continue uploading files if one already exists. (Only valid when uploading to PyPI. Other implementations
+            may not support this.)
+
         --universal2
             Control whether to build universal2 wheel for macOS or not. Only applies to macOS targets, do nothing
             otherwise
diff --git a/src/main.rs b/src/main.rs
index 2fcba726d..24819f091 100644
--- a/src/main.rs
+++ b/src/main.rs
@@ -147,6 +147,10 @@ struct PublishOpt {
     /// Do not strip the library for minimum file size
     #[structopt(long = "no-strip")]
     no_strip: bool,
+    /// Continue uploading files if one already exists.
+    /// (Only valid when uploading to PyPI. Other implementations may not support this.)
+    #[structopt(long = "skip-existing")]
+    skip_existing: bool,
 }
 
 #[derive(Debug, StructOpt)]
@@ -423,12 +427,21 @@ fn upload_ui(build: BuildOptions, publish: &PublishOpt, no_sdist: bool) -> Resul
                 bail!("Username and/or password are wrong");
             }
             Err(err) => {
+                let filename = wheel_path.file_name().unwrap_or(&wheel_path.as_os_str());
+                if let UploadError::FileExistsError(_) = err {
+                    if publish.skip_existing {
+                        eprintln!(
+                            "⚠  Skipping {:?} because it appears to already exist",
+                            filename
+                        );
+                        continue;
+                    }
+                }
                 let filesize = fs::metadata(&wheel_path)
                     .map(|x| ByteSize(x.len()).to_string())
                     .unwrap_or_else(|e| {
                         format!("Failed to get the filesize of {:?}: {}", &wheel_path, e)
                     });
-                let filename = wheel_path.file_name().unwrap_or(&wheel_path.as_os_str());
                 return Err(err)
                     .context(format!("💥 Failed to upload {:?} ({})", filename, filesize));
             }
diff --git a/src/upload.rs b/src/upload.rs
index 20d08bc91..94023a4f3 100644
--- a/src/upload.rs
+++ b/src/upload.rs
@@ -29,6 +29,9 @@ pub enum UploadError {
     /// The registry returned something else than 200
     #[error("Failed to upload the wheel with status {0}: {1}")]
     StatusCodeError(String, String),
+    /// File already exists
+    #[error("File already exists: {0}")]
+    FileExistsError(String),
 }
 
 impl From<io::Error> for UploadError {
@@ -95,18 +98,38 @@ pub fn upload(
         .basic_auth(registry.username.clone(), Some(registry.password.clone()))
         .send()?;
 
-    if response.status().is_success() {
-        Ok(())
-    } else if response.status() == StatusCode::FORBIDDEN {
-        Err(UploadError::AuthenticationError)
+    let status = response.status();
+    if status.is_success() {
+        return Ok(());
+    }
+    let err_text = response.text().unwrap_or_else(|e| {
+        format!(
+            "The registry should return some text, even in case of an error, but didn't ({})",
+            e
+        )
+    });
+    // Detect FileExistsError the way twine does
+    // https://github.com/pypa/twine/blob/87846e5777b380d4704704a69e1f9a7a1231451c/twine/commands/upload.py#L30
+    if status == StatusCode::FORBIDDEN {
+        if err_text.contains("overwrite artifact") {
+            // Artifactory (https://jfrog.com/artifactory/)
+            Err(UploadError::FileExistsError(err_text))
+        } else {
+            Err(UploadError::AuthenticationError)
+        }
     } else {
-        let status_string = response.status().to_string();
-        let err_text = response.text().unwrap_or_else(|e| {
-            format!(
-                "The registry should return some text, even in case of an error, but didn't ({})",
-                e
-            )
-        });
-        Err(UploadError::StatusCodeError(status_string, err_text))
+        let status_string = status.to_string();
+        if status == StatusCode::CONFLICT // pypiserver (https://pypi.org/project/pypiserver)
+            // PyPI / TestPyPI
+            || (status == StatusCode::BAD_REQUEST && err_text.contains("already exists"))
+            // Nexus Repository OSS (https://www.sonatype.com/nexus-repository-oss)
+            || (status == StatusCode::BAD_REQUEST && err_text.contains("updating asset"))
+            // # Gitlab Enterprise Edition (https://about.gitlab.com)
+            || (status == StatusCode::BAD_REQUEST && err_text.contains("already been taken"))
+        {
+            Err(UploadError::FileExistsError(err_text))
+        } else {
+            Err(UploadError::StatusCodeError(status_string, err_text))
+        }
     }
 }