diff --git a/main.go b/main.go
index 27eed19..1de492e 100644
--- a/main.go
+++ b/main.go
@@ -191,7 +191,6 @@ func mainLoop(ctx context.Context, invocationClient *client.InvocationClient, ba
 		select {
 		case <-ctx.Done():
 			// We're already done
-			util.Logln(ctx.Err())
 			return eventCounter, ""
 		default:
 			// Our call to next blocks. It is likely that the container is frozen immediately after we call NextEvent.
@@ -201,7 +200,6 @@ func mainLoop(ctx context.Context, invocationClient *client.InvocationClient, ba
 			eventStart := time.Now()
 
 			if err != nil {
-
 				util.Logln(err)
 				err = invocationClient.ExitError(ctx, "NextEventError.Main", err)
 				if err != nil {
@@ -224,7 +222,6 @@ func mainLoop(ctx context.Context, invocationClient *client.InvocationClient, ba
 					util.Logf("We suspected a timeout for request %s but got telemetry anyway", lastRequestId)
 				default:
 				}
-
 			}
 
 			invokedFunctionARN = event.InvokedFunctionARN
@@ -260,16 +257,19 @@ func mainLoop(ctx context.Context, invocationClient *client.InvocationClient, ba
 
 			// Set the timeout timer for a smidge before the actual timeout;
 			// we can recover from early.
-			timeoutWatchBegins := time.Millisecond * 100
-			timeout := timeoutInstant.Sub(time.Now()) - timeoutWatchBegins
+			timeoutWatchBegins := 100 * time.Millisecond
+			hardTimeout := timeoutInstant.Sub(time.Now())
+			softTimeout := hardTimeout - timeoutWatchBegins
+
+			hardCtx, hardCancel := context.WithTimeout(ctx, hardTimeout)
+			defer hardCancel()
 
-			invCtx, cancel := context.WithTimeout(ctx, timeout)
-			defer cancel()
+			softCtx, softCancel := context.WithTimeout(hardCtx, softTimeout)
+			defer softCancel()
 
 			select {
-			case <-invCtx.Done():
+			case <-softCtx.Done():
 				// We are about to timeout
-				util.Debugln("Timeout suspected: ", invCtx.Err())
 				probablyTimeout = true
 				continue
 			case telemetryBytes := <-telemetryChan:
@@ -282,7 +282,7 @@ func mainLoop(ctx context.Context, invocationClient *client.InvocationClient, ba
 
 				pollLogServer(logServer, batch)
 				harvested := batch.Harvest(time.Now())
-				shipHarvest(ctx, harvested, telemetryClient, invokedFunctionARN)
+				shipHarvest(hardCtx, harvested, telemetryClient, invokedFunctionARN)
 			}
 
 			lastEventStart = eventStart
diff --git a/main_test.go b/main_test.go
index 74b0900..7115f96 100644
--- a/main_test.go
+++ b/main_test.go
@@ -3,10 +3,12 @@ package main
 import (
 	"context"
 	"encoding/json"
+	"fmt"
 	"net/http"
 	"net/http/httptest"
 	"os"
 	"testing"
+	"time"
 
 	"github.com/newrelic/newrelic-lambda-extension/lambda/extension/api"
 	"github.com/newrelic/newrelic-lambda-extension/util"
@@ -532,6 +534,117 @@ func TestMainTimeout(t *testing.T) {
 	assert.Equal(t, 1, nextEventRequestCount)
 }
 
+func TestMainTimeoutUnreachable(t *testing.T) {
+	ctx, cancel := context.WithTimeout(context.Background(), time.Duration(200*time.Millisecond))
+	defer cancel()
+	overrideContext(ctx)
+
+	srv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		defer util.Close(r.Body)
+
+		if r.URL.Path == "/2020-01-01/extension/register" {
+			w.Header().Add(api.ExtensionIdHeader, "test-ext-id")
+			w.WriteHeader(200)
+			res, err := json.Marshal(api.RegistrationResponse{
+				FunctionName:    "foobar",
+				FunctionVersion: "$latest",
+				Handler:         "lambda.handler",
+			})
+			assert.Nil(t, err)
+			_, _ = w.Write(res)
+		}
+
+		if r.URL.Path == "/2020-01-01/extension/init/error" {
+			w.WriteHeader(200)
+			_, _ = w.Write([]byte(""))
+		}
+
+		if r.URL.Path == "/2020-01-01/extension/exit/error" {
+			w.WriteHeader(200)
+			_, _ = w.Write(nil)
+		}
+
+		if r.URL.Path == "/2020-08-15/logs" {
+			w.WriteHeader(200)
+			_, _ = w.Write(nil)
+		}
+
+		if r.URL.Path == "/2020-01-01/extension/event/next" {
+			time.Sleep(25 * time.Millisecond)
+
+			w.WriteHeader(200)
+			res, err := json.Marshal(api.InvocationEvent{
+				EventType:          api.Invoke,
+				DeadlineMs:         100,
+				RequestID:          "12345",
+				InvokedFunctionARN: "arn:aws:lambda:us-east-1:12345:foobar",
+				ShutdownReason:     "",
+				Tracing:            nil,
+			})
+			assert.Nil(t, err)
+			_, _ = w.Write(res)
+		}
+
+		if r.URL.Path == "/aws/lambda/v1" {
+			time.Sleep(5 * time.Second)
+
+			w.WriteHeader(200)
+			_, _ = w.Write(nil)
+		}
+	}))
+	defer srv.Close()
+
+	url := srv.URL[7:]
+
+	_ = os.Setenv(api.LambdaHostPortEnvVar, url)
+	defer os.Unsetenv(api.LambdaHostPortEnvVar)
+
+	_ = os.Setenv("NEW_RELIC_LICENSE_KEY", "foobar")
+	defer os.Unsetenv("NEW_RELIC_LICENSE_KEY")
+
+	_ = os.Setenv("NEW_RELIC_LOG_SERVER_HOST", "localhost")
+	defer os.Unsetenv("NEW_RELIC_LOG_SERVER_HOST")
+
+	_ = os.Setenv("NEW_RELIC_EXTENSION_LOG_LEVEL", "DEBUG")
+	defer os.Unsetenv("NEW_RELIC_EXTENSION_LOG_LEVEL")
+
+	_ = os.Setenv("NEW_RELIC_TELEMETRY_ENDPOINT", fmt.Sprintf("%s/aws/lambda/v1", srv.URL))
+	defer os.Unsetenv("NEW_RELIC_TELEMETRY_ENDPOINT")
+
+	_ = os.Remove("/tmp/newrelic-telemetry")
+
+	go func() {
+		pipeOpened := false
+
+		for {
+			select {
+			case <-ctx.Done():
+				return
+			default:
+				if _, err := os.Stat("/tmp/newrelic-telemetry"); os.IsNotExist(err) {
+					if pipeOpened {
+						return
+					} else {
+						continue
+					}
+				} else {
+					pipeOpened = true
+				}
+
+				pipe, err := os.OpenFile("/tmp/newrelic-telemetry", os.O_WRONLY, 0)
+				assert.Nil(t, err)
+				defer pipe.Close()
+
+				pipe.WriteString("foobar\n")
+				pipe.Close()
+				time.Sleep(100 * time.Millisecond)
+			}
+		}
+	}()
+
+	assert.NotPanics(t, main)
+}
+
 func overrideContext(ctx context.Context) {
 	rootCtx = ctx
 }
diff --git a/telemetry/client.go b/telemetry/client.go
index 5070834..8d88147 100644
--- a/telemetry/client.go
+++ b/telemetry/client.go
@@ -177,6 +177,7 @@ func (c *Client) sendPayloads(compressedPayloads []*bytes.Buffer, builder reques
 			successCount += 1
 		}
 	}
+
 	return successCount, sentBytes, nil
 }