diff --git a/packages/dd-trace/src/config.js b/packages/dd-trace/src/config.js
index 7a92a611fcb..14bdd84b94d 100644
--- a/packages/dd-trace/src/config.js
+++ b/packages/dd-trace/src/config.js
@@ -145,7 +145,7 @@ function maybeFile (filepath) {
   try {
     return fs.readFileSync(filepath, 'utf8')
   } catch (e) {
-    log.error(e)
+    log.error('Error reading file %s', filepath, e)
     return undefined
   }
 }
@@ -378,7 +378,7 @@ class Config {
         } catch (e) {
           // Only log error if the user has set a git.properties path
           if (process.env.DD_GIT_PROPERTIES_FILE) {
-            log.error(e)
+            log.error('Error reading DD_GIT_PROPERTIES_FILE: %s', DD_GIT_PROPERTIES_FILE, e)
           }
         }
         if (gitPropertiesString) {
diff --git a/packages/dd-trace/src/datastreams/writer.js b/packages/dd-trace/src/datastreams/writer.js
index f8c9e021ecc..5f789f2e056 100644
--- a/packages/dd-trace/src/datastreams/writer.js
+++ b/packages/dd-trace/src/datastreams/writer.js
@@ -45,13 +45,13 @@ class DataStreamsWriter {
 
     zlib.gzip(encodedPayload, { level: 1 }, (err, compressedData) => {
       if (err) {
-        log.error(err)
+        log.error('Error zipping datastream', err)
         return
       }
       makeRequest(compressedData, this._url, (err, res) => {
         log.debug(`Response from the agent: ${res}`)
         if (err) {
-          log.error(err)
+          log.error('Error sending datastream', err)
         }
       })
     })
diff --git a/packages/dd-trace/src/dogstatsd.js b/packages/dd-trace/src/dogstatsd.js
index ba84de71341..a396c9e98a4 100644
--- a/packages/dd-trace/src/dogstatsd.js
+++ b/packages/dd-trace/src/dogstatsd.js
@@ -71,7 +71,7 @@ class DogStatsDClient {
     const buffer = Buffer.concat(queue)
     request(buffer, this._httpOptions, (err) => {
       if (err) {
-        log.error('HTTP error from agent: ' + err.stack)
+        log.error('DogStatsDClient: HTTP error from agent: %s', err.message, err)
         if (err.status === 404) {
           // Inside this if-block, we have connectivity to the agent, but
           // we're not getting a 200 from the proxy endpoint. If it's a 404,
@@ -89,7 +89,7 @@ class DogStatsDClient {
       this._sendUdpFromQueue(queue, this._host, this._family)
     } else {
       lookup(this._host, (err, address, family) => {
-        if (err) return log.error(err)
+        if (err) return log.error('DogStatsDClient: Host not found', err)
         this._sendUdpFromQueue(queue, address, family)
       })
     }
diff --git a/packages/dd-trace/src/exporters/agent/writer.js b/packages/dd-trace/src/exporters/agent/writer.js
index 82a28647778..8fac323e614 100644
--- a/packages/dd-trace/src/exporters/agent/writer.js
+++ b/packages/dd-trace/src/exporters/agent/writer.js
@@ -41,17 +41,17 @@ class Writer extends BaseWriter {
       startupLog({ agentError: err })
 
       if (err) {
-        log.error(err)
+        log.error('Error sending payload to the agent (status code: %s)', err.status, err)
         done()
         return
       }
 
-      log.debug(`Response from the agent: ${res}`)
+      log.debug('Response from the agent: %s', res)
 
       try {
         this._prioritySampler.update(JSON.parse(res).rate_by_service)
       } catch (e) {
-        log.error(e)
+        log.error('Error updating prioritySampler rates', e)
 
         runtimeMetrics.increment(`${METRIC_PREFIX}.errors`, true)
         runtimeMetrics.increment(`${METRIC_PREFIX}.errors.by.name`, `name:${e.name}`, true)
diff --git a/packages/dd-trace/src/exporters/span-stats/writer.js b/packages/dd-trace/src/exporters/span-stats/writer.js
index 3ece6d221b4..37cd6c77d5e 100644
--- a/packages/dd-trace/src/exporters/span-stats/writer.js
+++ b/packages/dd-trace/src/exporters/span-stats/writer.js
@@ -16,7 +16,7 @@ class Writer extends BaseWriter {
   _sendPayload (data, _, done) {
     makeRequest(data, this._url, (err, res) => {
       if (err) {
-        log.error(err)
+        log.error('Error sending span stats', err)
         done()
         return
       }
diff --git a/packages/dd-trace/src/opentracing/tracer.js b/packages/dd-trace/src/opentracing/tracer.js
index 2d854442cc3..4ae30ca93ac 100644
--- a/packages/dd-trace/src/opentracing/tracer.js
+++ b/packages/dd-trace/src/opentracing/tracer.js
@@ -91,7 +91,7 @@ class DatadogTracer {
       }
       this._propagators[format].inject(context, carrier)
     } catch (e) {
-      log.error(e)
+      log.error('Error injecting trace', e)
       runtimeMetrics.increment('datadog.tracer.node.inject.errors', true)
     }
   }
@@ -100,7 +100,7 @@ class DatadogTracer {
     try {
       return this._propagators[format].extract(carrier)
     } catch (e) {
-      log.error(e)
+      log.error('Error extracting trace', e)
       runtimeMetrics.increment('datadog.tracer.node.extract.errors', true)
       return null
     }
diff --git a/packages/dd-trace/src/proxy.js b/packages/dd-trace/src/proxy.js
index 5c113399601..7a6027f90f1 100644
--- a/packages/dd-trace/src/proxy.js
+++ b/packages/dd-trace/src/proxy.js
@@ -182,7 +182,7 @@ class Tracer extends NoopProxy {
         }
       }
     } catch (e) {
-      log.error(e)
+      log.error('Error initialising tracer', e)
     }
 
     return this
@@ -193,7 +193,7 @@ class Tracer extends NoopProxy {
     try {
       return require('./profiler').start(config)
     } catch (e) {
-      log.error(e)
+      log.error('Error starting profiler', e)
     }
   }
 
diff --git a/packages/dd-trace/src/runtime_metrics.js b/packages/dd-trace/src/runtime_metrics.js
index b2711879a05..49e724eb11c 100644
--- a/packages/dd-trace/src/runtime_metrics.js
+++ b/packages/dd-trace/src/runtime_metrics.js
@@ -32,7 +32,7 @@ module.exports = {
       nativeMetrics = require('@datadog/native-metrics')
       nativeMetrics.start()
     } catch (e) {
-      log.error(e)
+      log.error('Error starting native metrics', e)
       nativeMetrics = null
     }
 
diff --git a/packages/dd-trace/src/telemetry/send-data.js b/packages/dd-trace/src/telemetry/send-data.js
index 813fa427812..81406910c27 100644
--- a/packages/dd-trace/src/telemetry/send-data.js
+++ b/packages/dd-trace/src/telemetry/send-data.js
@@ -57,7 +57,7 @@ function sendData (config, application, host, reqType, payload = {}, cb = () =>
     try {
       url = url || new URL(getAgentlessTelemetryEndpoint(config.site))
     } catch (err) {
-      log.error(err)
+      log.error('Telemetry endpoint url is invalid', err)
       // No point to do the request if the URL is invalid
       return cb(err, { payload, reqType })
     }
@@ -100,7 +100,7 @@ function sendData (config, application, host, reqType, payload = {}, cb = () =>
         path: '/api/v2/apmtelemetry'
       }
       if (backendUrl) {
-        request(data, backendOptions, (error) => { log.error(error) })
+        request(data, backendOptions, (error) => { log.error('Error sending telemetry data', error) })
       } else {
         log.error('Invalid Telemetry URL')
       }
diff --git a/packages/dd-trace/test/config.spec.js b/packages/dd-trace/test/config.spec.js
index 9c255d722bd..1eba985d04b 100644
--- a/packages/dd-trace/test/config.spec.js
+++ b/packages/dd-trace/test/config.spec.js
@@ -1781,9 +1781,12 @@ describe('Config', () => {
     })
 
     expect(log.error).to.be.callCount(3)
-    expect(log.error.firstCall).to.have.been.calledWithExactly(error)
-    expect(log.error.secondCall).to.have.been.calledWithExactly(error)
-    expect(log.error.thirdCall).to.have.been.calledWithExactly(error)
+    expect(log.error.firstCall)
+      .to.have.been.calledWithExactly('Error reading file %s', 'DOES_NOT_EXIST.json', error)
+    expect(log.error.secondCall)
+      .to.have.been.calledWithExactly('Error reading file %s', 'DOES_NOT_EXIST.html', error)
+    expect(log.error.thirdCall)
+      .to.have.been.calledWithExactly('Error reading file %s', 'DOES_NOT_EXIST.json', error)
 
     expect(config.appsec.enabled).to.be.true
     expect(config.appsec.rules).to.eq('path/to/rules.json')
diff --git a/packages/dd-trace/test/exporters/agent/writer.spec.js b/packages/dd-trace/test/exporters/agent/writer.spec.js
index ce7a62d49bf..aad8749ef37 100644
--- a/packages/dd-trace/test/exporters/agent/writer.spec.js
+++ b/packages/dd-trace/test/exporters/agent/writer.spec.js
@@ -149,6 +149,7 @@ function describeWriter (protocolVersion) {
 
     it('should log request errors', done => {
       const error = new Error('boom')
+      error.status = 42
 
       request.yields(error)
 
@@ -156,7 +157,8 @@ function describeWriter (protocolVersion) {
       writer.flush()
 
       setTimeout(() => {
-        expect(log.error).to.have.been.calledWith(error)
+        expect(log.error)
+          .to.have.been.calledWith('Error sending payload to the agent (status code: %s)', error.status, error)
         done()
       })
     })
diff --git a/packages/dd-trace/test/exporters/span-stats/writer.spec.js b/packages/dd-trace/test/exporters/span-stats/writer.spec.js
index d65d480409d..f8e65500e04 100644
--- a/packages/dd-trace/test/exporters/span-stats/writer.spec.js
+++ b/packages/dd-trace/test/exporters/span-stats/writer.spec.js
@@ -106,7 +106,7 @@ describe('span-stats writer', () => {
         encoder.count.returns(1)
 
         writer.flush(() => {
-          expect(log.error).to.have.been.calledWith(error)
+          expect(log.error).to.have.been.calledWith('Error sending span stats', error)
           done()
         })
       })
diff --git a/packages/dd-trace/test/proxy.spec.js b/packages/dd-trace/test/proxy.spec.js
index 4836e99787f..dd145390245 100644
--- a/packages/dd-trace/test/proxy.spec.js
+++ b/packages/dd-trace/test/proxy.spec.js
@@ -520,8 +520,9 @@ describe('TracerProxy', () => {
         const profilerImportFailureProxy = new ProfilerImportFailureProxy()
         profilerImportFailureProxy.init()
 
+        sinon.assert.calledOnce(log.error)
         const expectedErr = sinon.match.instanceOf(Error).and(sinon.match.has('code', 'MODULE_NOT_FOUND'))
-        sinon.assert.calledWith(log.error, sinon.match(expectedErr))
+        sinon.assert.match(log.error.firstCall.lastArg, sinon.match(expectedErr))
       })
 
       it('should start telemetry', () => {