diff --git a/app/models/ci/build.rb b/app/models/ci/build.rb
index 5c1168e8ef5..889f8ce27a6 100644
--- a/app/models/ci/build.rb
+++ b/app/models/ci/build.rb
@@ -221,9 +221,7 @@ module Ci
 
         build.deployment&.drop
 
-        next if build.retries_max.zero?
-
-        if build.retries_count < build.retries_max
+        if build.retry_failure?
           begin
             Ci::Build.retry(build, build.user)
           rescue Gitlab::Access::AccessDeniedError => ex
@@ -321,7 +319,17 @@ module Ci
     end
 
     def retries_max
-      self.options.to_h.fetch(:retry, 0).to_i
+      normalized_retry.fetch(:max, 0)
+    end
+
+    def retry_when
+      normalized_retry.fetch(:when, ['always'])
+    end
+
+    def retry_failure?
+      return false if retries_max.zero? || retries_count >= retries_max
+
+      retry_when.include?('always') || retry_when.include?(failure_reason.to_s)
     end
 
     def latest?
@@ -886,6 +894,16 @@ module Ci
       options&.dig(:environment, :url) || persisted_environment&.external_url
     end
 
+    # The format of the retry option changed in GitLab 11.5: Before it was
+    # integer only, after it is a hash. New builds are created with the new
+    # format, but builds created before GitLab 11.5 and saved in database still
+    # have the old integer only format. This method returns the retry option
+    # normalized as a hash in 11.5+ format.
+    def normalized_retry
+      value = options&.dig(:retry)
+      value.is_a?(Integer) ? { max: value } : value.to_h
+    end
+
     def build_attributes_from_config
       return {} unless pipeline.config_processor
 
diff --git a/changelogs/unreleased/max_retries_when.yml b/changelogs/unreleased/max_retries_when.yml
new file mode 100644
index 00000000000..dad3cd8a123
--- /dev/null
+++ b/changelogs/unreleased/max_retries_when.yml
@@ -0,0 +1,5 @@
+---
+title: Allow to configure when to retry failed CI jobs
+merge_request: 21758
+author: Markus Doits
+type: added
diff --git a/doc/ci/yaml/README.md b/doc/ci/yaml/README.md
index b3a55e48f4e..c827faace33 100644
--- a/doc/ci/yaml/README.md
+++ b/doc/ci/yaml/README.md
@@ -74,7 +74,7 @@ A job is defined by a list of parameters that define the job behavior.
 | after_script  | no       | Override a set of commands that are executed after job |
 | environment   | no       | Defines a name of environment to which deployment is done by this job |
 | coverage      | no       | Define code coverage settings for a given job |
-| retry         | no       | Define how many times a job can be auto-retried in case of a failure |
+| retry         | no       | Define when and how many times a job can be auto-retried in case of a failure |
 | parallel      | no       | Defines how many instances of a job should be run in parallel |
 
 ### `extends`
@@ -1433,18 +1433,20 @@ job1:
 ## `retry`
 
 > [Introduced][ce-12909] in GitLab 9.5.
+> [Behaviour expanded](https://gitlab.com/gitlab-org/gitlab-ce/merge_requests/21758)
+> in GitLab 11.5 to control on which failures to retry.
 
 `retry` allows you to configure how many times a job is going to be retried in
 case of a failure.
 
-When a job fails, and has `retry` configured it is going to be processed again
+When a job fails and has `retry` configured, it is going to be processed again
 up to the amount of times specified by the `retry` keyword.
 
 If `retry` is set to 2, and a job succeeds in a second run (first retry), it won't be retried
 again. `retry` value has to be a positive integer, equal or larger than 0, but
 lower or equal to 2 (two retries maximum, three runs in total).
 
-A simple example:
+A simple example to retry in all failure cases:
 
 ```yaml
 test:
@@ -1452,6 +1454,57 @@ test:
   retry: 2
 ```
 
+By default, a job will be retried on all failure cases. To have a better control
+on which failures to retry, `retry` can be a hash with with the following keys:
+
+- `max`: The maximum number of retries.
+- `when`: The failure cases to retry.
+
+To retry only runner system failures at maximum two times:
+
+```yaml
+test:
+  script: rspec
+  retry:
+    max: 2
+    when: runner_system_failure
+```
+
+If there is another failure, other than a runner system failure, the job will
+not be retried.
+
+To retry on multiple failure cases, `when` can also be an array of failures:
+
+```yaml
+test:
+  script: rspec
+  retry:
+    max: 2
+    when:
+      - runner_system_failure
+      - stuck_or_timeout_failure
+```
+
+Possible values for `when` are:
+
+<!--
+  Please make sure to update `RETRY_WHEN_IN_DOCUMENTATION` array in
+  `spec/lib/gitlab/ci/config/entry/retry_spec.rb` if you change any of
+  the documented values below. The test there makes sure that all documented
+  values are really valid as a config option and therefore should always
+  stay in sync with this documentation.
+ -->
+
+- `always`: Retry on any failure (default).
+- `unknown_failure`: Retry when the failure reason is unknown.
+- `script_failure`: Retry when the script failed.
+- `api_failure`: Retry on API failure.
+- `stuck_or_timeout_failure`: Retry when the job got stuck or timed out.
+- `runner_system_failure`: Retry if there was a runner system failure (e.g. setting up the job failed).
+- `missing_dependency_failure`: Retry if a dependency was missing.
+- `runner_unsupported`: Retry if the runner was unsupported.
+
+
 ## `parallel`
 
 > [Introduced](https://gitlab.com/gitlab-org/gitlab-ce/merge_requests/22631) in GitLab 11.5.
diff --git a/lib/gitlab/ci/config/entry/job.rb b/lib/gitlab/ci/config/entry/job.rb
index 362014b1a09..8e8c979f973 100644
--- a/lib/gitlab/ci/config/entry/job.rb
+++ b/lib/gitlab/ci/config/entry/job.rb
@@ -26,16 +26,12 @@ module Gitlab
             with_options allow_nil: true do
               validates :tags, array_of_strings: true
               validates :allow_failure, boolean: true
-              validates :retry, numericality: { only_integer: true,
-                                                greater_than_or_equal_to: 0,
-                                                less_than_or_equal_to: 2 }
               validates :parallel, numericality: { only_integer: true,
                                                    greater_than_or_equal_to: 2 }
               validates :when,
                 inclusion: { in: %w[on_success on_failure always manual delayed],
                              message: 'should be on_success, on_failure, ' \
                                       'always, manual or delayed' }
-
               validates :dependencies, array_of_strings: true
               validates :extends, type: String
             end
@@ -86,6 +82,9 @@ module Gitlab
           entry :coverage, Entry::Coverage,
             description: 'Coverage configuration for this job.'
 
+          entry :retry, Entry::Retry,
+               description: 'Retry configuration for this job.'
+
           helpers :before_script, :script, :stage, :type, :after_script,
                   :cache, :image, :services, :only, :except, :variables,
                   :artifacts, :commands, :environment, :coverage, :retry,
@@ -160,7 +159,7 @@ module Gitlab
               environment: environment_defined? ? environment_value : nil,
               environment_name: environment_defined? ? environment_value[:name] : nil,
               coverage: coverage_defined? ? coverage_value : nil,
-              retry: retry_defined? ? retry_value.to_i : nil,
+              retry: retry_defined? ? retry_value : nil,
               parallel: parallel_defined? ? parallel_value.to_i : nil,
               artifacts: artifacts_value,
               after_script: after_script_value,
diff --git a/lib/gitlab/ci/config/entry/retry.rb b/lib/gitlab/ci/config/entry/retry.rb
new file mode 100644
index 00000000000..e39cc5de229
--- /dev/null
+++ b/lib/gitlab/ci/config/entry/retry.rb
@@ -0,0 +1,90 @@
+module Gitlab
+  module Ci
+    class Config
+      module Entry
+        ##
+        # Entry that represents a retry config for a job.
+        #
+        class Retry < Simplifiable
+          strategy :SimpleRetry, if: -> (config) { config.is_a?(Integer) }
+          strategy :FullRetry, if: -> (config) { config.is_a?(Hash) }
+
+          class SimpleRetry < Entry::Node
+            include Entry::Validatable
+
+            validations do
+              validates :config, numericality: { only_integer: true,
+                                                 greater_than_or_equal_to: 0,
+                                                 less_than_or_equal_to: 2 }
+            end
+
+            def value
+              {
+                max: config
+              }
+            end
+
+            def location
+              'retry'
+            end
+          end
+
+          class FullRetry < Entry::Node
+            include Entry::Validatable
+            include Entry::Attributable
+
+            ALLOWED_KEYS = %i[max when].freeze
+            attributes :max, :when
+
+            validations do
+              validates :config, allowed_keys: ALLOWED_KEYS
+
+              with_options allow_nil: true do
+                validates :max, numericality: { only_integer: true,
+                                                greater_than_or_equal_to: 0,
+                                                less_than_or_equal_to: 2 }
+
+                validates :when, array_of_strings_or_string: true
+                validates :when,
+                          allowed_array_values: { in: FullRetry.possible_retry_when_values },
+                          if: -> (config) { config.when.is_a?(Array) }
+                validates :when,
+                          inclusion: { in: FullRetry.possible_retry_when_values },
+                          if: -> (config) { config.when.is_a?(String) }
+              end
+            end
+
+            def self.possible_retry_when_values
+              @possible_retry_when_values ||= ::Ci::Build.failure_reasons.keys.map(&:to_s) + ['always']
+            end
+
+            def value
+              super.tap do |config|
+                # make sure that `when` is an array, because we allow it to
+                # be passed as a String in config for simplicity
+                config[:when] = Array.wrap(config[:when]) if config[:when]
+              end
+            end
+
+            def location
+              'retry'
+            end
+          end
+
+          class UnknownStrategy < Entry::Node
+            def errors
+              ["#{location} has to be either an integer or a hash"]
+            end
+
+            def location
+              'retry config'
+            end
+          end
+
+          def self.default
+          end
+        end
+      end
+    end
+  end
+end
diff --git a/lib/gitlab/ci/config/entry/validators.rb b/lib/gitlab/ci/config/entry/validators.rb
index 805d26ca8d8..a1d552fb2e5 100644
--- a/lib/gitlab/ci/config/entry/validators.rb
+++ b/lib/gitlab/ci/config/entry/validators.rb
@@ -7,11 +7,11 @@ module Gitlab
         module Validators
           class AllowedKeysValidator < ActiveModel::EachValidator
             def validate_each(record, attribute, value)
-              unknown_keys = record.config.try(:keys).to_a - options[:in]
+              unknown_keys = value.try(:keys).to_a - options[:in]
 
               if unknown_keys.any?
-                record.errors.add(:config, 'contains unknown keys: ' +
-                                            unknown_keys.join(', '))
+                record.errors.add(attribute, "contains unknown keys: " +
+                                             unknown_keys.join(', '))
               end
             end
           end
@@ -24,6 +24,16 @@ module Gitlab
             end
           end
 
+          class AllowedArrayValuesValidator < ActiveModel::EachValidator
+            def validate_each(record, attribute, value)
+              unkown_values = value - options[:in]
+              unless unkown_values.empty?
+                record.errors.add(attribute, "contains unknown values: " +
+                                              unkown_values.join(', '))
+              end
+            end
+          end
+
           class ArrayOfStringsValidator < ActiveModel::EachValidator
             include LegacyValidationHelpers
 
@@ -68,6 +78,14 @@ module Gitlab
             end
           end
 
+          class HashOrIntegerValidator < ActiveModel::EachValidator
+            def validate_each(record, attribute, value)
+              unless value.is_a?(Hash) || value.is_a?(Integer)
+                record.errors.add(attribute, 'should be a hash or an integer')
+              end
+            end
+          end
+
           class KeyValidator < ActiveModel::EachValidator
             include LegacyValidationHelpers
 
diff --git a/spec/lib/gitlab/ci/config/entry/job_spec.rb b/spec/lib/gitlab/ci/config/entry/job_spec.rb
index f1a2946acda..ac9b0c674a5 100644
--- a/spec/lib/gitlab/ci/config/entry/job_spec.rb
+++ b/spec/lib/gitlab/ci/config/entry/job_spec.rb
@@ -10,7 +10,7 @@ describe Gitlab::Ci::Config::Entry::Job do
       let(:result) do
         %i[before_script script stage type after_script cache
            image services only except variables artifacts
-           environment coverage]
+           environment coverage retry]
       end
 
       it { is_expected.to match_array result }
@@ -98,45 +98,6 @@ describe Gitlab::Ci::Config::Entry::Job do
         end
       end
 
-      context 'when retry value is not correct' do
-        context 'when it is not a numeric value' do
-          let(:config) { { retry: true } }
-
-          it 'returns error about invalid type' do
-            expect(entry).not_to be_valid
-            expect(entry.errors).to include 'job retry is not a number'
-          end
-        end
-
-        context 'when it is lower than zero' do
-          let(:config) { { retry: -1 } }
-
-          it 'returns error about value too low' do
-            expect(entry).not_to be_valid
-            expect(entry.errors)
-              .to include 'job retry must be greater than or equal to 0'
-          end
-        end
-
-        context 'when it is not an integer' do
-          let(:config) { { retry: 1.5 } }
-
-          it 'returns error about wrong value' do
-            expect(entry).not_to be_valid
-            expect(entry.errors).to include 'job retry must be an integer'
-          end
-        end
-
-        context 'when the value is too high' do
-          let(:config) { { retry: 10 } }
-
-          it 'returns error about value too high' do
-            expect(entry).not_to be_valid
-            expect(entry.errors).to include 'job retry must be less than or equal to 2'
-          end
-        end
-      end
-
       context 'when parallel value is not correct' do
         context 'when it is not a numeric value' do
           let(:config) { { parallel: true } }
diff --git a/spec/lib/gitlab/ci/config/entry/retry_spec.rb b/spec/lib/gitlab/ci/config/entry/retry_spec.rb
new file mode 100644
index 00000000000..164a9ed4c3d
--- /dev/null
+++ b/spec/lib/gitlab/ci/config/entry/retry_spec.rb
@@ -0,0 +1,236 @@
+require 'spec_helper'
+
+describe Gitlab::Ci::Config::Entry::Retry do
+  let(:entry) { described_class.new(config) }
+
+  shared_context 'when retry value is a numeric', :numeric do
+    let(:config) { max }
+    let(:max) {}
+  end
+
+  shared_context 'when retry value is a hash', :hash do
+    let(:config) { { max: max, when: public_send(:when) }.compact }
+    let(:when) {}
+    let(:max) {}
+  end
+
+  describe '#value' do
+    subject(:value) { entry.value }
+
+    context 'when retry value is a numeric', :numeric do
+      let(:max) { 2 }
+
+      it 'is returned as a hash with max key' do
+        expect(value).to eq(max: 2)
+      end
+    end
+
+    context 'when retry value is a hash', :hash do
+      context 'and `when` is a string' do
+        let(:when) { 'unknown_failure' }
+
+        it 'returns when wrapped in an array' do
+          expect(value).to eq(when: ['unknown_failure'])
+        end
+      end
+
+      context 'and `when` is an array' do
+        let(:when) { %w[unknown_failure runner_system_failure] }
+
+        it 'returns when as it was passed' do
+          expect(value).to eq(when: %w[unknown_failure runner_system_failure])
+        end
+      end
+    end
+  end
+
+  describe 'validation' do
+    context 'when retry value is correct' do
+      context 'when it is a numeric', :numeric do
+        let(:max) { 2 }
+
+        it 'is valid' do
+          expect(entry).to be_valid
+        end
+      end
+
+      context 'when it is a hash', :hash do
+        context 'with max' do
+          let(:max) { 2 }
+
+          it 'is valid' do
+            expect(entry).to be_valid
+          end
+        end
+
+        context 'with string when' do
+          let(:when) { 'unknown_failure' }
+
+          it 'is valid' do
+            expect(entry).to be_valid
+          end
+        end
+
+        context 'with string when always' do
+          let(:when) { 'always' }
+
+          it 'is valid' do
+            expect(entry).to be_valid
+          end
+        end
+
+        context 'with array when' do
+          let(:when) { %w[unknown_failure runner_system_failure] }
+
+          it 'is valid' do
+            expect(entry).to be_valid
+          end
+        end
+
+        # Those values are documented at `doc/ci/yaml/README.md`. If any of
+        # those values gets invalid, documentation must be updated. To make
+        # sure this is catched, check explicitly that all of the documented
+        # values are valid. If they are not it means the documentation and this
+        # array must be updated.
+        RETRY_WHEN_IN_DOCUMENTATION = %w[
+            always
+            unknown_failure
+            script_failure
+            api_failure
+            stuck_or_timeout_failure
+            runner_system_failure
+            missing_dependency_failure
+            runner_unsupported
+        ].freeze
+
+        RETRY_WHEN_IN_DOCUMENTATION.each do |reason|
+          context "with when from documentation `#{reason}`" do
+            let(:when) { reason }
+
+            it 'is valid' do
+              expect(entry).to be_valid
+            end
+          end
+        end
+
+        ::Ci::Build.failure_reasons.each_key do |reason|
+          context "with when from CommitStatus.failure_reasons `#{reason}`" do
+            let(:when) { reason }
+
+            it 'is valid' do
+              expect(entry).to be_valid
+            end
+          end
+        end
+      end
+    end
+
+    context 'when retry value is not correct' do
+      context 'when it is not a numeric nor an array' do
+        let(:config) { true }
+
+        it 'returns error about invalid type' do
+          expect(entry).not_to be_valid
+          expect(entry.errors).to include 'retry config has to be either an integer or a hash'
+        end
+      end
+
+      context 'when it is a numeric', :numeric do
+        context 'when it is lower than zero' do
+          let(:max) { -1 }
+
+          it 'returns error about value too low' do
+            expect(entry).not_to be_valid
+            expect(entry.errors)
+              .to include 'retry config must be greater than or equal to 0'
+          end
+        end
+
+        context 'when it is not an integer' do
+          let(:max) { 1.5 }
+
+          it 'returns error about wrong value' do
+            expect(entry).not_to be_valid
+            expect(entry.errors).to include 'retry config has to be either an integer or a hash'
+          end
+        end
+
+        context 'when the value is too high' do
+          let(:max) { 10 }
+
+          it 'returns error about value too high' do
+            expect(entry).not_to be_valid
+            expect(entry.errors).to include 'retry config must be less than or equal to 2'
+          end
+        end
+      end
+
+      context 'when it is a hash', :hash do
+        context 'with unknown keys' do
+          let(:config) { { max: 2, unknown_key: :something, one_more: :key } }
+
+          it 'returns error about the unknown key' do
+            expect(entry).not_to be_valid
+            expect(entry.errors)
+              .to include 'retry config contains unknown keys: unknown_key, one_more'
+          end
+        end
+
+        context 'with max lower than zero' do
+          let(:max) { -1 }
+
+          it 'returns error about value too low' do
+            expect(entry).not_to be_valid
+            expect(entry.errors)
+              .to include 'retry max must be greater than or equal to 0'
+          end
+        end
+
+        context 'with max not an integer' do
+          let(:max) { 1.5 }
+
+          it 'returns error about wrong value' do
+            expect(entry).not_to be_valid
+            expect(entry.errors).to include 'retry max must be an integer'
+          end
+        end
+
+        context 'iwth max too high' do
+          let(:max) { 10 }
+
+          it 'returns error about value too high' do
+            expect(entry).not_to be_valid
+            expect(entry.errors).to include 'retry max must be less than or equal to 2'
+          end
+        end
+
+        context 'with when in wrong format' do
+          let(:when) { true }
+
+          it 'returns error about the wrong format' do
+            expect(entry).not_to be_valid
+            expect(entry.errors).to include 'retry when should be an array of strings or a string'
+          end
+        end
+
+        context 'with an unknown when string' do
+          let(:when) { 'unknown_reason' }
+
+          it 'returns error about the wrong format' do
+            expect(entry).not_to be_valid
+            expect(entry.errors).to include 'retry when is not included in the list'
+          end
+        end
+
+        context 'with an unknown failure reason in a when array' do
+          let(:when) { %w[unknown_reason runner_system_failure] }
+
+          it 'returns error about the wrong format' do
+            expect(entry).not_to be_valid
+            expect(entry.errors).to include 'retry when contains unknown values: unknown_reason'
+          end
+        end
+      end
+    end
+  end
+end
diff --git a/spec/lib/gitlab/ci/yaml_processor_spec.rb b/spec/lib/gitlab/ci/yaml_processor_spec.rb
index dcfd54107a3..441e8214181 100644
--- a/spec/lib/gitlab/ci/yaml_processor_spec.rb
+++ b/spec/lib/gitlab/ci/yaml_processor_spec.rb
@@ -53,11 +53,11 @@ module Gitlab
         describe 'retry entry' do
           context 'when retry count is specified' do
             let(:config) do
-              YAML.dump(rspec: { script: 'rspec', retry: 1 })
+              YAML.dump(rspec: { script: 'rspec', retry: { max: 1 } })
             end
 
             it 'includes retry count in build options attribute' do
-              expect(subject[:options]).to include(retry: 1)
+              expect(subject[:options]).to include(retry: { max: 1 })
             end
           end
 
diff --git a/spec/models/ci/build_spec.rb b/spec/models/ci/build_spec.rb
index 5bd2f096656..6849bc6db7a 100644
--- a/spec/models/ci/build_spec.rb
+++ b/spec/models/ci/build_spec.rb
@@ -1472,15 +1472,15 @@ describe Ci::Build do
     end
 
     describe '#retries_max' do
-      context 'when max retries value is defined' do
-        subject { create(:ci_build, options: { retry: 1 }) }
+      context 'with retries max config option' do
+        subject { create(:ci_build, options: { retry: { max: 1 } }) }
 
-        it 'returns a number of configured max retries' do
+        it 'returns the number of configured max retries' do
           expect(subject.retries_max).to eq 1
         end
       end
 
-      context 'when max retries value is not defined' do
+      context 'without retries max config option' do
         subject { create(:ci_build) }
 
         it 'returns zero' do
@@ -1495,6 +1495,104 @@ describe Ci::Build do
           expect(subject.retries_max).to eq 0
         end
       end
+
+      context 'with integer only config option' do
+        subject { create(:ci_build, options: { retry: 1 }) }
+
+        it 'returns the number of configured max retries' do
+          expect(subject.retries_max).to eq 1
+        end
+      end
+    end
+
+    describe '#retry_when' do
+      context 'with retries when config option' do
+        subject { create(:ci_build, options: { retry: { when: ['some_reason'] } }) }
+
+        it 'returns the configured when' do
+          expect(subject.retry_when).to eq ['some_reason']
+        end
+      end
+
+      context 'without retries when config option' do
+        subject { create(:ci_build) }
+
+        it 'returns always array' do
+          expect(subject.retry_when).to eq ['always']
+        end
+      end
+
+      context 'with integer only config option' do
+        subject { create(:ci_build, options: { retry: 1 }) }
+
+        it 'returns always array' do
+          expect(subject.retry_when).to eq ['always']
+        end
+      end
+    end
+
+    describe '#retry_failure?' do
+      subject { create(:ci_build) }
+
+      context 'when retries max is zero' do
+        before do
+          expect(subject).to receive(:retries_max).at_least(:once).and_return(0)
+        end
+
+        it 'returns false' do
+          expect(subject.retry_failure?).to eq false
+        end
+      end
+
+      context 'when retries max equals retries count' do
+        before do
+          expect(subject).to receive(:retries_max).at_least(:once).and_return(1)
+          expect(subject).to receive(:retries_count).at_least(:once).and_return(1)
+        end
+
+        it 'returns false' do
+          expect(subject.retry_failure?).to eq false
+        end
+      end
+
+      context 'when retries max is higher than retries count' do
+        before do
+          expect(subject).to receive(:retries_max).at_least(:once).and_return(2)
+          expect(subject).to receive(:retries_count).at_least(:once).and_return(1)
+        end
+
+        context 'and retry when is always' do
+          before do
+            expect(subject).to receive(:retry_when).at_least(:once).and_return(['always'])
+          end
+
+          it 'returns true' do
+            expect(subject.retry_failure?).to eq true
+          end
+        end
+
+        context 'and retry when includes the failure_reason' do
+          before do
+            expect(subject).to receive(:failure_reason).at_least(:once).and_return('some_reason')
+            expect(subject).to receive(:retry_when).at_least(:once).and_return(['some_reason'])
+          end
+
+          it 'returns true' do
+            expect(subject.retry_failure?).to eq true
+          end
+        end
+
+        context 'and retry when does not include failure_reason' do
+          before do
+            expect(subject).to receive(:failure_reason).at_least(:once).and_return('some_reason')
+            expect(subject).to receive(:retry_when).at_least(:once).and_return(['some', 'other failure'])
+          end
+
+          it 'returns false' do
+            expect(subject.retry_failure?).to eq false
+          end
+        end
+      end
     end
   end
 
@@ -2887,7 +2985,7 @@ describe Ci::Build do
     end
 
     context 'when build is configured to be retried' do
-      subject { create(:ci_build, :running, options: { retry: 3 }, project: project, user: user) }
+      subject { create(:ci_build, :running, options: { retry: { max: 3 } }, project: project, user: user) }
 
       it 'retries build and assigns the same user to it' do
         expect(described_class).to receive(:retry)
diff --git a/spec/services/ci/create_pipeline_service_spec.rb b/spec/services/ci/create_pipeline_service_spec.rb
index 054b7b1561c..5c87ed5c3c6 100644
--- a/spec/services/ci/create_pipeline_service_spec.rb
+++ b/spec/services/ci/create_pipeline_service_spec.rb
@@ -435,16 +435,34 @@ describe Ci::CreatePipelineService do
     end
 
     context 'when builds with auto-retries are configured' do
-      before do
-        config = YAML.dump(rspec: { script: 'rspec', retry: 2 })
-        stub_ci_pipeline_yaml_file(config)
+      context 'as an integer' do
+        before do
+          config = YAML.dump(rspec: { script: 'rspec', retry: 2 })
+          stub_ci_pipeline_yaml_file(config)
+        end
+
+        it 'correctly creates builds with auto-retry value configured' do
+          pipeline = execute_service
+
+          expect(pipeline).to be_persisted
+          expect(pipeline.builds.find_by(name: 'rspec').retries_max).to eq 2
+          expect(pipeline.builds.find_by(name: 'rspec').retry_when).to eq ['always']
+        end
       end
 
-      it 'correctly creates builds with auto-retry value configured' do
-        pipeline = execute_service
+      context 'as hash' do
+        before do
+          config = YAML.dump(rspec: { script: 'rspec', retry: { max: 2, when: 'runner_system_failure' } })
+          stub_ci_pipeline_yaml_file(config)
+        end
 
-        expect(pipeline).to be_persisted
-        expect(pipeline.builds.find_by(name: 'rspec').retries_max).to eq 2
+        it 'correctly creates builds with auto-retry value configured' do
+          pipeline = execute_service
+
+          expect(pipeline).to be_persisted
+          expect(pipeline.builds.find_by(name: 'rspec').retries_max).to eq 2
+          expect(pipeline.builds.find_by(name: 'rspec').retry_when).to eq ['runner_system_failure']
+        end
       end
     end
 
diff --git a/spec/services/ci/process_pipeline_service_spec.rb b/spec/services/ci/process_pipeline_service_spec.rb
index 8c7258c42ad..538992b621e 100644
--- a/spec/services/ci/process_pipeline_service_spec.rb
+++ b/spec/services/ci/process_pipeline_service_spec.rb
@@ -671,9 +671,9 @@ describe Ci::ProcessPipelineService, '#execute' do
 
   context 'when builds with auto-retries are configured' do
     before do
-      create_build('build:1', stage_idx: 0, user: user, options: { retry: 2 })
+      create_build('build:1', stage_idx: 0, user: user, options: { retry: { max: 2 } })
       create_build('test:1', stage_idx: 1, user: user, when: :on_failure)
-      create_build('test:2', stage_idx: 1, user: user, options: { retry: 1 })
+      create_build('test:2', stage_idx: 1, user: user, options: { retry: { max: 1 } })
     end
 
     it 'automatically retries builds in a valid order' do