diff --git a/cli/src/commands/mod.rs b/cli/src/commands/mod.rs
index 9f03a12f12..daa926d67a 100644
--- a/cli/src/commands/mod.rs
+++ b/cli/src/commands/mod.rs
@@ -95,6 +95,11 @@ pub enum SourcemapCommand {
         /// Whether to delete the source map files after uploading them
         #[arg(long, default_value = "false")]
         delete_after: bool,
+
+        /// Whether to skip SSL verification when uploading chunks - only use when using self-signed certificates for 
+        /// self-deployed instances
+        #[arg(long, default_value = "false")]
+        skip_ssl_verification: bool,
     },
 }
 
@@ -131,6 +136,7 @@ impl Cli {
                     project,
                     version,
                     delete_after,
+                    skip_ssl_verification,
                 } => {
                     sourcemap::inject::inject(directory)?;
                     sourcemap::upload::upload(
@@ -139,6 +145,7 @@ impl Cli {
                         project.clone(),
                         version.clone(),
                         *delete_after,
+                        *skip_ssl_verification,
                     )?;
                 }
             },
diff --git a/cli/src/commands/sourcemap/upload.rs b/cli/src/commands/sourcemap/upload.rs
index ca1fc40c66..29f9415ffa 100644
--- a/cli/src/commands/sourcemap/upload.rs
+++ b/cli/src/commands/sourcemap/upload.rs
@@ -51,6 +51,7 @@ pub fn upload(
     project: Option<String>,
     version: Option<String>,
     delete_after: bool,
+    skip_ssl_verification: bool,
 ) -> Result<()> {
     let token = load_token().context("While starting upload command")?;
     let host = token.get_host(host.as_deref());
@@ -83,10 +84,17 @@ pub fn upload(
         Some(content_hash(uploads.iter().map(|upload| &upload.data))),
         project,
         version,
+        skip_ssl_verification,
     )
     .context("While creating release")?;
 
-    upload_chunks(&base_url, &token.token, uploads, release.as_ref())?;
+    upload_chunks(
+        &base_url,
+        &token.token,
+        uploads,
+        release.as_ref(),
+        skip_ssl_verification,
+    )?;
 
     if delete_after {
         delete_files(sourcemap_paths).context("While deleting sourcemaps")?;
@@ -110,8 +118,12 @@ fn upload_chunks(
     token: &str,
     uploads: Vec<ChunkUpload>,
     release: Option<&CreateReleaseResponse>,
+    skip_ssl_verification: bool,
 ) -> Result<()> {
-    let client = reqwest::blocking::Client::new();
+    let client = reqwest::blocking::Client::builder()
+        .danger_accept_invalid_certs(skip_ssl_verification)
+        .build()?;
+
     let release_id = release.map(|r| r.id.to_string());
     let chunk_ids = uploads
         .iter()
diff --git a/cli/src/utils/release.rs b/cli/src/utils/release.rs
index 148f20fed8..86f3cbb330 100644
--- a/cli/src/utils/release.rs
+++ b/cli/src/utils/release.rs
@@ -30,6 +30,7 @@ pub fn create_release(
     hash_id: Option<String>,
     project: Option<String>,
     version: Option<String>,
+    skip_ssl_verification: bool,
 ) -> Result<Option<CreateReleaseResponse>> {
     let git_info = get_git_info(dir)?;
 
@@ -63,7 +64,9 @@ pub fn create_release(
         host, token.env_id
     );
 
-    let client = reqwest::blocking::Client::new();
+    let client = reqwest::blocking::Client::builder()
+        .danger_accept_invalid_certs(skip_ssl_verification)
+        .build()?;
 
     let response = client
         .post(&url)