diff --git a/packages/datadog-instrumentations/src/jest.js b/packages/datadog-instrumentations/src/jest.js
index 2b9b8d6bd2b..16874cfa055 100644
--- a/packages/datadog-instrumentations/src/jest.js
+++ b/packages/datadog-instrumentations/src/jest.js
@@ -313,11 +313,19 @@ function getWrappedEnvironment (BaseEnvironment, jestVersion) {
         const asyncResource = asyncResources.get(event.test)
 
         if (status === 'fail') {
-          log.warn('Setting probe because test failed')
+          const shouldSetProbe = this.isDiEnabled && willBeRetried && numTestExecutions === 1
+          log.warn(
+            `Setting probe because test failed: ${getJestTestName(event.test)},
+num test executions: ${numTestExecutions}
+will be retried: ${willBeRetried}
+is di enabled: ${this.isDiEnabled}
+should set probe: ${shouldSetProbe}
+`
+          )
           asyncResource.runInAsyncScope(() => {
             testErrCh.publish({
               error: formatJestError(event.test.errors[0]),
-              shouldSetProbe: this.isDiEnabled && willBeRetried && numTestExecutions === 1,
+              shouldSetProbe,
               promises
             })
           })
@@ -333,7 +341,9 @@ function getWrappedEnvironment (BaseEnvironment, jestVersion) {
           })
         }
 
+        const shouldRemoveProbe = this.isDiEnabled && !willBeRetried
         asyncResource.runInAsyncScope(() => {
+          log.warn(`shouldRemoveProbe: ${shouldRemoveProbe}`)
           testFinishCh.publish({
             status,
             testStartLine: getTestLineStart(event.test.asyncError, this.testSuite),
diff --git a/packages/datadog-plugin-jest/src/index.js b/packages/datadog-plugin-jest/src/index.js
index 667e8569782..98b0d2318d1 100644
--- a/packages/datadog-plugin-jest/src/index.js
+++ b/packages/datadog-plugin-jest/src/index.js
@@ -24,7 +24,8 @@ const {
   TEST_IS_RUM_ACTIVE,
   TEST_BROWSER_DRIVER,
   getFormattedError,
-  TEST_RETRY_REASON
+  TEST_RETRY_REASON,
+  TEST_NAME
 } = require('../../dd-trace/src/plugins/util/test')
 const { COMPONENT } = require('../../dd-trace/src/constants')
 const id = require('../../dd-trace/src/id')
@@ -348,6 +349,7 @@ class JestPlugin extends CiPlugin {
       finishAllTraceSpans(span)
       this.activeTestSpan = null
       if (shouldRemoveProbe && this.runningTestProbeId) {
+        log.warn(`ci:jest:test:finish removing probe ${spanTags[TEST_NAME]}`)
         promises.isProbeRemoved = withTimeout(this.removeDiProbe(this.runningTestProbeId), 2000)
         this.runningTestProbeId = null
       }