diff --git a/lib/datadog/core/telemetry/logging.rb b/lib/datadog/core/telemetry/logging.rb
index ed040c9de50..eba7e87719c 100644
--- a/lib/datadog/core/telemetry/logging.rb
+++ b/lib/datadog/core/telemetry/logging.rb
@@ -2,6 +2,8 @@
 
 require_relative 'event'
 
+require 'pathname'
+
 module Datadog
   module Core
     module Telemetry
@@ -23,9 +25,7 @@ module Logging
 
         # Extract datadog stack trace from the exception
         module DatadogStackTrace
-          # Typically, `lib` is under `#{gem_name}-#{version}/`
-          # but not the case when providing a bundler custom path in `Gemfile`
-          REGEX = %r{/lib/datadog/}.freeze
+          GEM_ROOT = Pathname.new("#{__dir__}/../../../..").cleanpath.to_s
 
           def self.from(exception)
             backtrace = exception.backtrace
@@ -35,12 +35,12 @@ def self.from(exception)
 
             stack_trace = +''
             backtrace.each do |line|
-              stack_trace << if line.match?(REGEX)
-                               # Removing host related information
-                               line.sub(/^.*?(#{REGEX})/o, '\1') << ','
+              stack_trace << if line.start_with?(GEM_ROOT)
+                               line[GEM_ROOT.length..-1] || ''
                              else
-                               'REDACTED,'
+                               'REDACTED'
                              end
+              stack_trace << ','
             end
 
             stack_trace.chomp(',')
diff --git a/sig/datadog/core/telemetry/logging.rbs b/sig/datadog/core/telemetry/logging.rbs
index 324ac7112c4..57cd4ae8d37 100644
--- a/sig/datadog/core/telemetry/logging.rbs
+++ b/sig/datadog/core/telemetry/logging.rbs
@@ -3,7 +3,8 @@ module Datadog
     module Telemetry
       module Logging
         module DatadogStackTrace
-          REGEX: Regexp
+          GEM_ROOT: String
+
           def self.from: (Exception exception) -> String?
         end
 
diff --git a/spec/datadog/core/telemetry/logging_spec.rb b/spec/datadog/core/telemetry/logging_spec.rb
index 880c7c90a71..d96668d0c8b 100644
--- a/spec/datadog/core/telemetry/logging_spec.rb
+++ b/spec/datadog/core/telemetry/logging_spec.rb
@@ -130,10 +130,12 @@
     end
 
     it 'returns redacted stack trace' do
+      gem_root = Datadog::Core::Telemetry::Logging::DatadogStackTrace::GEM_ROOT
+
       exception = StandardError.new('Yo!')
       exception.set_backtrace(
         [
-          '/usr/local/bundle/gems/datadog-2.3.0.beta1/lib/datadog/core/telemetry/logging.rb:1 in `report`',
+          "#{gem_root}/lib/datadog/core/telemetry/logging.rb:1 in `report`",
           '/foo/bar/baz.rb:1 in `baz`',
           '/foo/bar.rb:1 in `bar`',
           '/foo.rb:1 in `foo`',