diff --git a/changes/fix-logging-of-errors b/changes/fix-logging-of-errors
new file mode 100644
index 0000000000..2c647ec10f
--- /dev/null
+++ b/changes/fix-logging-of-errors
@@ -0,0 +1 @@
+* Fix logging of errors in fleet serve.
diff --git a/server/contexts/logging/logging.go b/server/contexts/logging/logging.go
index 7dc1c460ea..7f4d2a33e2 100644
--- a/server/contexts/logging/logging.go
+++ b/server/contexts/logging/logging.go
@@ -110,13 +110,24 @@ func (l *LoggingContext) Log(ctx context.Context, logger kitlog.Logger) {
 	}
 
 	if len(l.Errs) > 0 {
-		var errs []string
-		var internalErrs []string
+		// Going for string concatenation here instead of json.Marshal mostly to not have to deal with error handling
+		// within this method. kitlog doesn't support slices of strings
+		var errs string
+		var internalErrs string
+		separator := " || "
 		for _, err := range l.Errs {
 			if e, ok := err.(fleet.ErrWithInternal); ok {
-				internalErrs = append(internalErrs, e.Internal())
+				if internalErrs == "" {
+					internalErrs = e.Internal()
+				} else {
+					internalErrs += separator + e.Internal()
+				}
 			} else {
-				errs = append(errs, err.Error())
+				if errs == "" {
+					errs = err.Error()
+				} else {
+					errs += separator + err.Error()
+				}
 			}
 		}
 		if len(errs) > 0 {
diff --git a/server/contexts/logging/logging_test.go b/server/contexts/logging/logging_test.go
new file mode 100644
index 0000000000..53eb593a2a
--- /dev/null
+++ b/server/contexts/logging/logging_test.go
@@ -0,0 +1,43 @@
+package logging
+
+import (
+	"bytes"
+	"context"
+	"strings"
+	"testing"
+
+	kitlog "github.com/go-kit/kit/log"
+	"github.com/pkg/errors"
+	"github.com/stretchr/testify/assert"
+)
+
+func TestLoggingErrs(t *testing.T) {
+	setupTest := func() (*bytes.Buffer, kitlog.Logger, *LoggingContext, context.Context) {
+		buf := new(bytes.Buffer)
+		logger := kitlog.NewLogfmtLogger(buf)
+		lc := &LoggingContext{}
+		ctx := NewContext(context.Background(), lc)
+		return buf, logger, lc, ctx
+	}
+	checkLogEnds := func(t *testing.T, logLine string, expected string) bool {
+		return assert.True(t, strings.HasSuffix(strings.TrimSpace(logLine), expected), logLine)
+	}
+
+	t.Run("one error", func(t *testing.T) {
+		buf, logger, lc, ctx := setupTest()
+
+		WithErr(ctx, errors.Wrap(errors.New("AAAA"), "BLAH"))
+		lc.Log(ctx, logger)
+		logLine := buf.String()
+		checkLogEnds(t, logLine, `err="BLAH: AAAA"`)
+	})
+	t.Run("two errors", func(t *testing.T) {
+		buf, logger, lc, ctx := setupTest()
+
+		WithErr(ctx, errors.Wrap(errors.New("AAAA"), "BLAH"))
+		WithErr(ctx, errors.Wrap(errors.New("BBBB"), "FOO"))
+		lc.Log(ctx, logger)
+		logLine := buf.String()
+		checkLogEnds(t, logLine, `err="BLAH: AAAA || FOO: BBBB"`)
+	})
+}
diff --git a/server/service/integration_logger_test.go b/server/service/integration_logger_test.go
index 2f39f97496..c2e76e9e9a 100644
--- a/server/service/integration_logger_test.go
+++ b/server/service/integration_logger_test.go
@@ -182,5 +182,5 @@ func (s *integrationLoggerTestSuite) TestEnrollAgentLogsErrors() {
 	require.Len(t, parts, 1)
 	logData := make(map[string]json.RawMessage)
 	require.NoError(t, json.Unmarshal([]byte(parts[0]), &logData))
-	assert.Equal(t, json.RawMessage(`["enroll failed: no matching secret found"]`), logData["err"])
+	assert.Equal(t, json.RawMessage(`"enroll failed: no matching secret found"`), logData["err"])
 }
diff --git a/server/service/service_osquery_test.go b/server/service/service_osquery_test.go
index 0c1a71869c..b78fad43c9 100644
--- a/server/service/service_osquery_test.go
+++ b/server/service/service_osquery_test.go
@@ -1664,8 +1664,8 @@ func TestDistributedQueriesLogsManyErrors(t *testing.T) {
 	require.Len(t, parts, 1)
 	logData := make(map[string]json.RawMessage)
 	require.NoError(t, json.Unmarshal([]byte(parts[0]), &logData))
-	assert.Equal(t, json.RawMessage(`["something went wrong"]`), logData["err"])
-	assert.Equal(t, json.RawMessage(`["Missing authorization check"]`), logData["internal"])
+	assert.Equal(t, json.RawMessage(`"something went wrong"`), logData["err"])
+	assert.Equal(t, json.RawMessage(`"Missing authorization check"`), logData["internal"])
 }
 
 func TestDistributedQueriesReloadsHostIfDetailsAreIn(t *testing.T) {