diff --git a/docs/docs/20-usage/20-pipeline-syntax.md b/docs/docs/20-usage/20-pipeline-syntax.md
index a7a64de678..64a22ca8ab 100644
--- a/docs/docs/20-usage/20-pipeline-syntax.md
+++ b/docs/docs/20-usage/20-pipeline-syntax.md
@@ -264,7 +264,20 @@ For more details check the [secrets docs](/docs/usage/secrets/).
 
 ### `when` - Conditional Execution
 
-Woodpecker supports defining conditions for pipeline step by a `when` block. If all conditions in the `when` block evaluate to true the step is executed, otherwise it is skipped.
+Woodpecker supports defining a list of conditions for a pipeline step by using a `when` block. If at least one of the conditions in the `when` block evaluate to true the step is executed, otherwise it is skipped. A condition can be a check like:
+
+```diff
+ pipeline:
+   slack:
+     image: plugins/slack
+     settings:
+       channel: dev
++    when:
++      - event: pull_request
++        repo: test/test
++      - event: push
++        branch: main
+```
 
 #### `repo`
 
@@ -277,7 +290,7 @@ Example conditional execution by repository:
      settings:
        channel: dev
 +    when:
-+      repo: test/test
++      - repo: test/test
 ```
 
 #### `branch`
@@ -295,7 +308,7 @@ pipeline:
     settings:
       channel: dev
 +   when:
-+     branch: master
++     - branch: master
 ```
 
 > The step now triggers on master, but also if the target branch of a pull request is `master`. Add an event condition to limit it further to pushes on master only.
@@ -304,23 +317,23 @@ Execute a step if the branch is `master` or `develop`:
 
 ```diff
 when:
-  branch: [master, develop]
+  - branch: [master, develop]
 ```
 
 Execute a step if the branch starts with `prefix/*`:
 
 ```diff
 when:
-  branch: prefix/*
+  - branch: prefix/*
 ```
 
 Execute a step using custom include and exclude logic:
 
 ```diff
 when:
-  branch:
-    include: [ master, release/* ]
-    exclude: [ release/1.0.0, release/1.1.* ]
+  - branch:
+      include: [ master, release/* ]
+      exclude: [ release/1.0.0, release/1.1.* ]
 ```
 
 #### `event`
@@ -329,29 +342,29 @@ Execute a step if the build event is a `tag`:
 
 ```diff
 when:
-  event: tag
+  - event: tag
 ```
 
 Execute a step if the pipeline event is a `push` to a specified branch:
 
 ```diff
 when:
-  event: push
-+ branch: main
+  - event: push
++   branch: main
 ```
 
 Execute a step for all non-pull request events:
 
 ```diff
 when:
-  event: [push, tag, deployment]
+  - event: [push, tag, deployment]
 ```
 
 Execute a step for all build events:
 
 ```diff
 when:
-  event: [push, pull_request, tag, deployment]
+  - event: [push, pull_request, tag, deployment]
 ```
 
 #### `tag`
@@ -361,8 +374,8 @@ Use glob expression to execute a step if the tag name starts with `v`:
 
 ```diff
 when:
-  event: tag
-  tag: v*
+  - event: tag
+    tag: v*
 ```
 
 #### `status`
@@ -376,7 +389,7 @@ pipeline:
     settings:
       channel: dev
 +   when:
-+     status: [ success, failure ]
++     - status: [ success, failure ]
 ```
 
 #### `platform`
@@ -389,14 +402,14 @@ Execute a step for a specific platform:
 
 ```diff
 when:
-  platform: linux/amd64
+  - platform: linux/amd64
 ```
 
 Execute a step for a specific platform using wildcards:
 
 ```diff
 when:
-  platform:  [ linux/*, windows/amd64 ]
+  - platform:  [ linux/*, windows/amd64 ]
 ```
 
 #### `environment`
@@ -405,8 +418,8 @@ Execute a step for deployment events matching the target deployment environment:
 
 ```diff
 when:
-  environment: production
-  event: deployment
+  - environment: production
+  - event: deployment
 ```
 
 #### `matrix`
@@ -415,9 +428,9 @@ Execute a step for a single matrix permutation:
 
 ```diff
 when:
-  matrix:
-    GO_VERSION: 1.5
-    REDIS_VERSION: 2.8
+  - matrix:
+      GO_VERSION: 1.5
+      REDIS_VERSION: 2.8
 ```
 
 #### `instance`
@@ -426,7 +439,7 @@ Execute a step only on a certain Woodpecker instance matching the specified host
 
 ```diff
 when:
-  instance: stage.woodpecker.company.com
+  - instance: stage.woodpecker.company.com
 ```
 
 #### `path`
@@ -441,17 +454,17 @@ Execute a step only on a pipeline with certain files being changed:
 
 ```diff
 when:
-  path: "src/*"
+  - path: "src/*"
 ```
 
 You can use [glob patterns](https://github.com/bmatcuk/doublestar#patterns) to match the changed files and specify if the step should run if a file matching that pattern has been changed `include` or if some files have **not** been changed `exclude`.
 
 ```diff
 when:
-  path:
-    include: [ '.woodpecker/*.yml', '*.ini' ]
-    exclude: [ '*.md', 'docs/**' ]
-    ignore_message: "[ALL]"
+  - path:
+      include: [ '.woodpecker/*.yml', '*.ini' ]
+      exclude: [ '*.md', 'docs/**' ]
+      ignore_message: "[ALL]"
 ```
 
 **Hint:** Passing a defined ignore-message like `[ALL]` inside the commit message will ignore all path conditions.
diff --git a/pipeline/frontend/yaml/compiler/compiler.go b/pipeline/frontend/yaml/compiler/compiler.go
index d317d74dd7..a76be917a9 100644
--- a/pipeline/frontend/yaml/compiler/compiler.go
+++ b/pipeline/frontend/yaml/compiler/compiler.go
@@ -145,7 +145,7 @@ func (c *Compiler) Compile(conf *yaml.Config) *backend.Config {
 		config.Stages = append(config.Stages, stage)
 	} else if !c.local && !conf.SkipClone {
 		for i, container := range conf.Clone.Containers {
-			if !container.Constraints.Match(c.metadata) {
+			if !container.When.Match(c.metadata) {
 				continue
 			}
 			stage := new(backend.Stage)
@@ -172,7 +172,7 @@ func (c *Compiler) Compile(conf *yaml.Config) *backend.Config {
 		stage.Alias = nameServices
 
 		for i, container := range conf.Services.Containers {
-			if !container.Constraints.Match(c.metadata) {
+			if !container.When.Match(c.metadata) {
 				continue
 			}
 
@@ -188,11 +188,11 @@ func (c *Compiler) Compile(conf *yaml.Config) *backend.Config {
 	var group string
 	for i, container := range conf.Pipeline.Containers {
 		// Skip if local and should not run local
-		if c.local && !container.Constraints.Local.Bool() {
+		if c.local && !container.When.IsLocal() {
 			continue
 		}
 
-		if !container.Constraints.Match(c.metadata) {
+		if !container.When.Match(c.metadata) {
 			continue
 		}
 
diff --git a/pipeline/frontend/yaml/compiler/convert.go b/pipeline/frontend/yaml/compiler/convert.go
index 3e1fb6c5b5..ec426b10f2 100644
--- a/pipeline/frontend/yaml/compiler/convert.go
+++ b/pipeline/frontend/yaml/compiler/convert.go
@@ -145,6 +145,12 @@ func (c *Compiler) createProcess(name string, container *yaml.Container, section
 		cpuSet = c.reslimit.CPUSet
 	}
 
+	// all constraints must exclude success.
+	onSuccess := container.When.IsEmpty() ||
+		!container.When.ExcludesStatus("success")
+	// at least one constraint must include the status failure.
+	onFailure := container.When.IncludesStatus("failure")
+
 	return &backend.Step{
 		Name:         name,
 		Alias:        container.Name,
@@ -172,11 +178,9 @@ func (c *Compiler) createProcess(name string, container *yaml.Container, section
 		CPUShares:    cpuShares,
 		CPUSet:       cpuSet,
 		AuthConfig:   authConfig,
-		OnSuccess:    container.Constraints.Status.Match("success"),
-		OnFailure: (len(container.Constraints.Status.Include)+
-			len(container.Constraints.Status.Exclude) != 0) &&
-			container.Constraints.Status.Match("failure"),
-		NetworkMode: networkMode,
-		IpcMode:     ipcMode,
+		OnSuccess:    onSuccess,
+		OnFailure:    onFailure,
+		NetworkMode:  networkMode,
+		IpcMode:      ipcMode,
 	}
 }
diff --git a/pipeline/frontend/yaml/config_test.go b/pipeline/frontend/yaml/config_test.go
index 92888e3f97..14deae65ef 100644
--- a/pipeline/frontend/yaml/config_test.go
+++ b/pipeline/frontend/yaml/config_test.go
@@ -61,10 +61,10 @@ func TestParse(t *testing.T) {
 				}
 				g.Assert(out.Pipeline.Containers[0].Name).Equal("notify_fail")
 				g.Assert(out.Pipeline.Containers[0].Image).Equal("plugins/slack")
-				g.Assert(len(out.Pipeline.Containers[0].Constraints.Event.Include)).Equal(0)
+				g.Assert(len(out.Pipeline.Containers[0].When.Constraints)).Equal(0)
 				g.Assert(out.Pipeline.Containers[1].Name).Equal("notify_success")
 				g.Assert(out.Pipeline.Containers[1].Image).Equal("plugins/slack")
-				g.Assert(out.Pipeline.Containers[1].Constraints.Event.Include).Equal([]string{"success"})
+				g.Assert(out.Pipeline.Containers[1].When.Constraints[0].Event.Include).Equal([]string{"success"})
 			})
 		})
 	})
diff --git a/pipeline/frontend/yaml/constraint/constraint.go b/pipeline/frontend/yaml/constraint/constraint.go
index 22c4d284f8..b363112f32 100644
--- a/pipeline/frontend/yaml/constraint/constraint.go
+++ b/pipeline/frontend/yaml/constraint/constraint.go
@@ -12,8 +12,13 @@ import (
 )
 
 type (
-	// Constraints defines a set of runtime constraints.
-	Constraints struct {
+	// When defines a set of runtime constraints.
+	When struct {
+		// If true then read from a list of constraint
+		Constraints []Constraint
+	}
+
+	Constraint struct {
 		Ref         List
 		Repo        List
 		Instance    List
@@ -47,9 +52,82 @@ type (
 	}
 )
 
+func (when *When) IsEmpty() bool {
+	return len(when.Constraints) == 0
+}
+
+// Returns true if at least one of the internal constraints is true.
+func (when *When) Match(metadata frontend.Metadata) bool {
+	for _, c := range when.Constraints {
+		if c.Match(metadata) {
+			return true
+		}
+	}
+	return when.IsEmpty()
+}
+
+func (when *When) IncludesStatus(status string) bool {
+	for _, c := range when.Constraints {
+		if c.Status.Includes(status) {
+			return true
+		}
+	}
+
+	return false
+}
+
+func (when *When) ExcludesStatus(status string) bool {
+	for _, c := range when.Constraints {
+		if !c.Status.Excludes(status) {
+			return false
+		}
+	}
+
+	return len(when.Constraints) > 0
+}
+
+// False if (any) non local
+func (when *When) IsLocal() bool {
+	for _, c := range when.Constraints {
+		if !c.Local.Bool() {
+			return false
+		}
+	}
+	return true
+}
+
+func (when *When) UnmarshalYAML(value *yaml.Node) error {
+	unmarshelAsList := func() error {
+		lst := []Constraint{}
+		err := value.Decode(&lst)
+		if err != nil {
+			return err
+		}
+		when.Constraints = lst
+		return nil
+	}
+
+	unmarshelAsDict := func() error {
+		c := Constraint{}
+		err := value.Decode(&c)
+		if err != nil {
+			return err
+		}
+		when.Constraints = append(when.Constraints, c)
+		return nil
+	}
+
+	err := unmarshelAsList()
+	if err != nil {
+		err = unmarshelAsDict()
+	}
+
+	return err
+}
+
 // Match returns true if all constraints match the given input. If a single
 // constraint fails a false value is returned.
-func (c *Constraints) Match(metadata frontend.Metadata) bool {
+func (c *Constraint) Match(metadata frontend.Metadata) bool {
 	match := c.Platform.Match(metadata.Sys.Platform) &&
 		c.Environment.Match(metadata.Curr.Target) &&
 		c.Event.Match(metadata.Curr.Event) &&
@@ -58,10 +136,11 @@ func (c *Constraints) Match(metadata frontend.Metadata) bool {
 		c.Instance.Match(metadata.Sys.Host) &&
 		c.Matrix.Match(metadata.Job.Matrix)
 
-	// changed files filter do only apply for pull-request and push events
+	// changed files filter apply only for pull-request and push events
 	if metadata.Curr.Event == frontend.EventPull || metadata.Curr.Event == frontend.EventPush {
 		match = match && c.Path.Match(metadata.Curr.Commit.ChangedFiles, metadata.Curr.Commit.Message)
 	}
+
 	if metadata.Curr.Event != frontend.EventTag {
 		match = match && c.Branch.Match(metadata.Curr.Commit.Branch)
 	}
@@ -137,6 +216,7 @@ func (c *Map) Match(params map[string]string) bool {
 	if len(c.Include) == 0 && len(c.Exclude) == 0 {
 		return true
 	}
+
 	// exclusions are processed first. So we can include everything and then
 	// selectively include others.
 	if len(c.Exclude) != 0 {
@@ -211,12 +291,13 @@ func (c *Path) UnmarshalYAML(value *yaml.Node) error {
 }
 
 // Match returns true if file paths in string slice matches the include and not exclude patterns
-//  or if commit message contains ignore message.
+// or if commit message contains ignore message.
 func (c *Path) Match(v []string, message string) bool {
 	// ignore file pattern matches if the commit message contains a pattern
 	if len(c.IgnoreMessage) > 0 && strings.Contains(strings.ToLower(message), strings.ToLower(c.IgnoreMessage)) {
 		return true
 	}
+
 	// always match if there are no commit files (empty commit)
 	if len(v) == 0 {
 		return true
diff --git a/pipeline/frontend/yaml/constraint/constraint_test.go b/pipeline/frontend/yaml/constraint/constraint_test.go
index 6a2d3ff3bd..94c364b18b 100644
--- a/pipeline/frontend/yaml/constraint/constraint_test.go
+++ b/pipeline/frontend/yaml/constraint/constraint_test.go
@@ -469,8 +469,8 @@ func TestConstraints(t *testing.T) {
 	}
 }
 
-func parseConstraints(t *testing.T, s string) *Constraints {
-	c := &Constraints{}
+func parseConstraints(t *testing.T, s string) *When {
+	c := &When{}
 	assert.NoError(t, yaml.Unmarshal([]byte(s), c))
 	return c
 }
diff --git a/pipeline/frontend/yaml/container.go b/pipeline/frontend/yaml/container.go
index 5e5287f69e..2e19537f6f 100644
--- a/pipeline/frontend/yaml/container.go
+++ b/pipeline/frontend/yaml/container.go
@@ -58,7 +58,7 @@ type (
 		Volumes       types.Volumes          `yaml:"volumes,omitempty"`
 		Secrets       Secrets                `yaml:"secrets,omitempty"`
 		Sysctls       types.SliceorMap       `yaml:"sysctls,omitempty"`
-		Constraints   constraint.Constraints `yaml:"when,omitempty"`
+		When          constraint.When        `yaml:"when,omitempty"`
 		Settings      map[string]interface{} `yaml:"settings"`
 	}
 )
diff --git a/pipeline/frontend/yaml/container_test.go b/pipeline/frontend/yaml/container_test.go
index 0ee54dd1e3..85fe82cc1d 100644
--- a/pipeline/frontend/yaml/container_test.go
+++ b/pipeline/frontend/yaml/container_test.go
@@ -109,9 +109,13 @@ func TestUnmarshalContainer(t *testing.T) {
 				{Source: "/etc/configs", Destination: "/etc/configs/", AccessMode: "ro"},
 			},
 		},
-		Constraints: constraint.Constraints{
-			Branch: constraint.List{
-				Include: []string{"master"},
+		When: constraint.When{
+			Constraints: []constraint.Constraint{
+				{
+					Branch: constraint.List{
+						Include: []string{"master"},
+					},
+				},
 			},
 		},
 		Settings: map[string]interface{}{
@@ -185,9 +189,13 @@ func TestUnmarshalContainers(t *testing.T) {
 						"tag":        stringsToInterface("next", "latest"),
 						"dry_run":    true,
 					},
-					Constraints: constraint.Constraints{
-						Event:  constraint.List{Include: []string{"push"}},
-						Branch: constraint.List{Include: []string{"${CI_REPO_DEFAULT_BRANCH}"}},
+					When: constraint.When{
+						Constraints: []constraint.Constraint{
+							{
+								Event:  constraint.List{Include: []string{"push"}},
+								Branch: constraint.List{Include: []string{"${CI_REPO_DEFAULT_BRANCH}"}},
+							},
+						},
 					},
 				},
 			},
@@ -213,9 +221,38 @@ func TestUnmarshalContainers(t *testing.T) {
 						"dockerfile": "docker/Dockerfile.cli",
 						"tag":        stringsToInterface("next"),
 					},
-					Constraints: constraint.Constraints{
-						Event:  constraint.List{Include: []string{"push"}},
-						Branch: constraint.List{Include: []string{"${CI_REPO_DEFAULT_BRANCH}"}},
+					When: constraint.When{
+						Constraints: []constraint.Constraint{
+							{
+								Event:  constraint.List{Include: []string{"push"}},
+								Branch: constraint.List{Include: []string{"${CI_REPO_DEFAULT_BRANCH}"}},
+							},
+						},
+					},
+				},
+			},
+		},
+		{
+			from: `publish-cli:
+    image: print/env
+    when:
+      - branch: ${CI_REPO_DEFAULT_BRANCH}
+        event: push
+      - event: pull_request`,
+			want: []*Container{
+				{
+					Name:  "publish-cli",
+					Image: "print/env",
+					When: constraint.When{
+						Constraints: []constraint.Constraint{
+							{
+								Event:  constraint.List{Include: []string{"push"}},
+								Branch: constraint.List{Include: []string{"${CI_REPO_DEFAULT_BRANCH}"}},
+							},
+							{
+								Event: constraint.List{Include: []string{"pull_request"}},
+							},
+						},
 					},
 				},
 			},
diff --git a/pipeline/schema/.woodpecker/test-when.yml b/pipeline/schema/.woodpecker/test-when.yml
index c3b95859ec..83f1a87ac4 100644
--- a/pipeline/schema/.woodpecker/test-when.yml
+++ b/pipeline/schema/.woodpecker/test-when.yml
@@ -111,3 +111,13 @@ pipeline:
       - echo "test"
     when:
       repo: test/test
+
+  when-multi:
+    image: alpine
+    commands:
+      - echo "test"
+    when:
+      - event: pull_request
+        repo: test/test
+      - event: push
+        branch: main
diff --git a/pipeline/schema/schema.json b/pipeline/schema/schema.json
index 6b3a509a57..5068647695 100644
--- a/pipeline/schema/schema.json
+++ b/pipeline/schema/schema.json
@@ -140,6 +140,18 @@
     },
     "step_when": {
       "description": "Steps can be skipped based on conditions. Read more: https://woodpecker-ci.org/docs/usage/pipeline-syntax#when---conditional-execution",
+      "oneOf": [
+        {
+          "type": "array",
+          "minLength": 1,
+          "items": { "$ref": "#/definitions/step_when_condition" }
+        },
+        {
+          "$ref": "#/definitions/step_when_condition"
+        }
+      ]
+    },
+    "step_when_condition": {
       "type": "object",
       "additionalProperties": false,
       "properties": {