diff --git a/src/commands/monitors/run.rs b/src/commands/monitors/run.rs
index 7ca4531fc5..db69aad663 100644
--- a/src/commands/monitors/run.rs
+++ b/src/commands/monitors/run.rs
@@ -140,7 +140,11 @@ fn execute_checkin(
     };
 
     let envelopes_api = EnvelopesApi::try_new()?;
-    envelopes_api.send_envelope(open_checkin)?;
+    
+    if let Err(e) = envelopes_api.send_envelope(open_checkin) {
+        log::error!("Failed to send in-progress check-in envelope: {e}");
+        log::info!("Continuing to run program...");
+    }
 
     let (success, code, elapsed) = run_program(args, monitor_slug);
 
@@ -161,7 +165,11 @@ fn execute_checkin(
         monitor_config: None,
     };
 
-    envelopes_api.send_envelope(close_checkin)?;
+    if let Err(e) = envelopes_api.send_envelope(close_checkin) {
+        log::error!("Failed to send final check-in envelope: {e}");
+        log::info!("Continuing to exit with program's exit code...");
+    }
+
     Ok((success, code))
 }
 
diff --git a/tests/integration/_cases/monitors/monitors-run-server-error-win.trycmd b/tests/integration/_cases/monitors/monitors-run-server-error-win.trycmd
new file mode 100644
index 0000000000..745aad7ac5
--- /dev/null
+++ b/tests/integration/_cases/monitors/monitors-run-server-error-win.trycmd
@@ -0,0 +1,8 @@
+```
+$ sentry-cli monitors run foo-monitor -- cmd.exe /C echo 123
+? success
+[..]ERROR[..]Failed to send in-progress check-in envelope[..]
+123
+[..]ERROR[..]Failed to send final check-in envelope[..]
+
+```
diff --git a/tests/integration/_cases/monitors/monitors-run-server-error.trycmd b/tests/integration/_cases/monitors/monitors-run-server-error.trycmd
new file mode 100644
index 0000000000..33d5c1cd4a
--- /dev/null
+++ b/tests/integration/_cases/monitors/monitors-run-server-error.trycmd
@@ -0,0 +1,8 @@
+```
+$ sentry-cli monitors run foo-monitor -- echo 123
+? success
+[..]ERROR[..]Failed to send in-progress check-in envelope[..]
+123
+[..]ERROR[..]Failed to send final check-in envelope[..]
+
+```
diff --git a/tests/integration/monitors/run.rs b/tests/integration/monitors/run.rs
index d8e72b69a9..206e3d3739 100644
--- a/tests/integration/monitors/run.rs
+++ b/tests/integration/monitors/run.rs
@@ -11,6 +11,18 @@ fn command_monitors_run() {
     }
 }
 
+#[test]
+fn command_monitors_run_server_error() {
+    let _server =
+        integration::mock_endpoint(EndpointOptions::new("POST", "/api/1337/envelope/", 500));
+
+    #[cfg(not(windows))]
+    integration::register_test("monitors/monitors-run-server-error.trycmd");
+
+    #[cfg(windows)]
+    integration::register_test("monitors/monitors-run-server-error-win.trycmd");
+}
+
 #[test]
 fn command_monitors_run_token_auth() {
     let _server = integration::mock_endpoint(