diff --git a/src/steps/sse.ts b/src/steps/sse.ts
index fc3587e..09e141c 100644
--- a/src/steps/sse.ts
+++ b/src/steps/sse.ts
@@ -60,6 +60,11 @@ export default async function (
 ) {
   const stepResult: StepRunResult = {
     type: 'sse',
+    request : {
+      url: params.url,
+      headers: params.headers,
+      size: 0,
+    }
   }
 
   const ssw = new co2()
@@ -81,18 +86,16 @@ export default async function (
     })
 
     const messages: MessageEvent[] = []
+    const expectedMessages: Set<string> | undefined = params.check?.messages
+      ? new Set(params.check?.messages?.map((m) => m.id))
+      : undefined
 
-    const timeout = setTimeout(() => {
+    // Closes the `EventSource` and exits as "passed"
+    const end = () => {
       ev.close()
 
       const messagesBuffer = Buffer.from(messages.map((m) => m.data).join('\n'))
 
-      stepResult.request = {
-        url: params.url,
-        headers: params.headers,
-        size: 0,
-      }
-
       stepResult.response = {
         contentType: 'text/event-stream',
         body: messagesBuffer,
@@ -103,12 +106,35 @@ export default async function (
       }
 
       resolve(true)
+    }
+
+    const timeout = setTimeout(() => {
+      console.debug('SSE timed out')
+      end()
     }, params.timeout || 10000)
 
     ev.onerror = (error) => {
       clearTimeout(timeout)
+
+      let message: string
+      if (ev.readyState === EventSource.CLOSED) {
+        // SSE stream closed gracefully
+        return end()
+      } else if (ev.readyState === EventSource.CONNECTING) {
+        // SSE stream closed by the server
+        if (expectedMessages === undefined) {
+          message = 'The SSE stream was closed by the server. If this is expected behavior, please use [`tests.<test>.steps.[step].sse.check.messages`](https://docs.stepci.com/reference/workflow-syntax.html#tests-test-steps-step-sse-check-messages-message).'
+        } else {
+          message = `The SSE stream was closed by the server before all expected messages were received. Missing IDs: ${JSON.stringify([...expectedMessages], null, 2)}`
+        }
+      } else {
+        // SSE stream is still open (`ev.readyState === EventSource.OPEN`)
+        // but received an "error" event from the server
+        message = `The SSE stream received an error event from the server: ${JSON.stringify(error, null, 2)}`
+      }
+
       ev.close()
-      reject(error)
+      reject({ ...error, message })
     }
 
     if (params.check) {
@@ -129,6 +155,9 @@ export default async function (
 
       if (params.check) {
         params.check.messages?.forEach((check, id) => {
+          // Don't run check if it's not intended for this message
+          if (check.id !== message.lastEventId) return
+
           if (check.body) {
             const result = checkResult(message.data, check.body)
             if (result.passed && stepResult.checks?.messages)
@@ -178,7 +207,7 @@ export default async function (
                 .map((c: CheckResult) => c.passed)
                 .every((passed) => passed)
 
-              if (passed && stepResult.checks?.messages)
+              if (stepResult.checks?.messages)
                 (stepResult.checks.messages as CheckResults)[check.id] = {
                   expected: check.jsonpath,
                   given: jsonpathResult,
@@ -190,6 +219,15 @@ export default async function (
           }
         })
       }
+
+      // Mark message as received
+      expectedMessages?.delete(message.lastEventId)
+      // If all expected messages have been received, close connection and return as "passed"
+      if (expectedMessages?.size === 0) {
+        // console.debug('All expected messages received, closing connection…')
+        clearTimeout(timeout)
+        end()
+      }
     }
   })