diff --git a/pipeline-model-definition/src/main/java/org/jenkinsci/plugins/pipeline/modeldefinition/when/impl/ChangeSetConditional.java b/pipeline-model-definition/src/main/java/org/jenkinsci/plugins/pipeline/modeldefinition/when/impl/ChangeSetConditional.java
index a6ddaf291..08553b80f 100644
--- a/pipeline-model-definition/src/main/java/org/jenkinsci/plugins/pipeline/modeldefinition/when/impl/ChangeSetConditional.java
+++ b/pipeline-model-definition/src/main/java/org/jenkinsci/plugins/pipeline/modeldefinition/when/impl/ChangeSetConditional.java
@@ -55,12 +55,14 @@ public class ChangeSetConditional extends DeclarativeStageConditional<ChangeSetC
     private transient String glob;
     private String pattern;
     private boolean caseSensitive;
+    private boolean shouldMatchAll;
     private String comparator;
 
     @DataBoundConstructor
     public ChangeSetConditional(String pattern) {
         this.pattern = pattern;
         this.caseSensitive = false;
+        this.shouldMatchAll = false;
     }
 
     @Deprecated
@@ -72,6 +74,10 @@ public boolean isCaseSensitive() {
         return caseSensitive;
     }
 
+    public boolean isShouldMatchAll() {
+        return shouldMatchAll;
+    }
+
     public String getPattern() {
         return pattern;
     }
@@ -107,10 +113,23 @@ public void setCaseSensitive(boolean caseSensitive) {
         this.caseSensitive = caseSensitive;
     }
 
-    public boolean changeSetMatches(ChangeLogSet.Entry change, String pattern, boolean caseSensitive) {
+    @DataBoundSetter
+    public void setShouldMatchAll(boolean shouldMatchAll) {
+        this.shouldMatchAll = shouldMatchAll;
+    }
+
+    public boolean changeSetMatches(ChangeLogSet.Entry change, String pattern, boolean caseSensitive, boolean shouldMatchAll) {
         Comparator c = Comparator.get(comparator, Comparator.GLOB);
+        if (shouldMatchAll) {
+            return change.getAffectedPaths().stream().allMatch(path -> c.compare(pattern, path, caseSensitive));
+        } else {
+            return change.getAffectedPaths().stream().anyMatch(path -> c.compare(pattern, path, caseSensitive));
+        }
+    }
 
-        return change.getAffectedPaths().stream().anyMatch(path -> c.compare(pattern, path, caseSensitive));
+    @Deprecated
+    public boolean changeSetMatches(ChangeLogSet.Entry change, String pattern, boolean caseSensitive) {
+        return changeSetMatches(change, pattern, caseSensitive, this.isShouldMatchAll());
     }
 
     @Extension
diff --git a/pipeline-model-definition/src/main/resources/org/jenkinsci/plugins/pipeline/modeldefinition/when/impl/AbstractChangelogConditionalScript.groovy b/pipeline-model-definition/src/main/resources/org/jenkinsci/plugins/pipeline/modeldefinition/when/impl/AbstractChangelogConditionalScript.groovy
index 12f4b00d2..683ad6b2e 100644
--- a/pipeline-model-definition/src/main/resources/org/jenkinsci/plugins/pipeline/modeldefinition/when/impl/AbstractChangelogConditionalScript.groovy
+++ b/pipeline-model-definition/src/main/resources/org/jenkinsci/plugins/pipeline/modeldefinition/when/impl/AbstractChangelogConditionalScript.groovy
@@ -81,15 +81,20 @@ abstract class AbstractChangelogConditionalScript<S extends DeclarativeStageCond
                 }
                 return false
             }
-            return changeSets.any {def set ->
-                return set.any { def change ->
-                    return matches(change)
-                }
-            }
+            return changeSetsMatches(changeSets);
         }
         return false
     }
 
     abstract boolean matches(ChangeLogSet.Entry change)
+
+    boolean changeSetsMatches(List<ChangeLogSet<? extends ChangeLogSet.Entry>> changeSets) {
+        return changeSets.any {def set ->
+            return set.any { def change ->
+                return matches(change)
+            }
+        }
+    }
+
     void initializeEval() {}
 }
diff --git a/pipeline-model-definition/src/main/resources/org/jenkinsci/plugins/pipeline/modeldefinition/when/impl/ChangeSetConditional/config.jelly b/pipeline-model-definition/src/main/resources/org/jenkinsci/plugins/pipeline/modeldefinition/when/impl/ChangeSetConditional/config.jelly
index e0f295337..6b2812b0c 100644
--- a/pipeline-model-definition/src/main/resources/org/jenkinsci/plugins/pipeline/modeldefinition/when/impl/ChangeSetConditional/config.jelly
+++ b/pipeline-model-definition/src/main/resources/org/jenkinsci/plugins/pipeline/modeldefinition/when/impl/ChangeSetConditional/config.jelly
@@ -35,5 +35,8 @@
         <f:entry field="comparator" title="Comparator">
             <f:select/>
         </f:entry>
+        <f:entry field="shouldMatchAll">
+            <f:checkbox title="whether all the elements in the changeset should match with the given pattern" checked="false"/>
+        </f:entry>
     </f:advanced>
 </j:jelly>
diff --git a/pipeline-model-definition/src/main/resources/org/jenkinsci/plugins/pipeline/modeldefinition/when/impl/ChangeSetConditional/help-shouldMatchAll.html b/pipeline-model-definition/src/main/resources/org/jenkinsci/plugins/pipeline/modeldefinition/when/impl/ChangeSetConditional/help-shouldMatchAll.html
new file mode 100644
index 000000000..93aefb890
--- /dev/null
+++ b/pipeline-model-definition/src/main/resources/org/jenkinsci/plugins/pipeline/modeldefinition/when/impl/ChangeSetConditional/help-shouldMatchAll.html
@@ -0,0 +1,27 @@
+<!--
+  ~ The MIT License
+  ~
+  ~ Copyright (c) 2019, Elasticsearch B.V.
+  ~
+  ~ Permission is hereby granted, free of charge, to any person obtaining a copy
+  ~ of this software and associated documentation files (the "Software"), to deal
+  ~ in the Software without restriction, including without limitation the rights
+  ~ to use, copy, modify, merge, publish, distribute, sublicense, and/or sell
+  ~ copies of the Software, and to permit persons to whom the Software is
+  ~ furnished to do so, subject to the following conditions:
+  ~
+  ~ The above copyright notice and this permission notice shall be included in
+  ~ all copies or substantial portions of the Software.
+  ~
+  ~ THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+  ~ IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
+  ~ FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
+  ~ AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
+  ~ LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,
+  ~ OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN
+  ~ THE SOFTWARE.
+  -->
+
+<p>
+    If true, the comparison should match all the elements in the changeset. Defaults to false.
+</p>
diff --git a/pipeline-model-definition/src/main/resources/org/jenkinsci/plugins/pipeline/modeldefinition/when/impl/ChangeSetConditionalScript.groovy b/pipeline-model-definition/src/main/resources/org/jenkinsci/plugins/pipeline/modeldefinition/when/impl/ChangeSetConditionalScript.groovy
index 2edb2b9b8..d037ce1d0 100644
--- a/pipeline-model-definition/src/main/resources/org/jenkinsci/plugins/pipeline/modeldefinition/when/impl/ChangeSetConditionalScript.groovy
+++ b/pipeline-model-definition/src/main/resources/org/jenkinsci/plugins/pipeline/modeldefinition/when/impl/ChangeSetConditionalScript.groovy
@@ -35,8 +35,21 @@ class ChangeSetConditionalScript extends AbstractChangelogConditionalScript<Chan
         super(s, c)
     }
 
+    @Override
+    boolean changeSetsMatches(List<ChangeLogSet<? extends ChangeLogSet.Entry>> changeSets) {
+        if (describable.shouldMatchAll) {
+            return changeSets.every { def set ->
+                return set.every { def change ->
+                    return matches(change)
+                }
+            }
+        } else {
+            super.changeSetsMatches(changeSets);
+        }
+    }
+
     @Override
     boolean matches(ChangeLogSet.Entry change) {
-        return describable.changeSetMatches(change, describable.pattern, describable.caseSensitive)
+        return describable.changeSetMatches(change, describable.pattern, describable.caseSensitive, describable.shouldMatchAll)
     }
 }
diff --git a/pipeline-model-definition/src/test/java/org/jenkinsci/plugins/pipeline/modeldefinition/WhenStageTest.java b/pipeline-model-definition/src/test/java/org/jenkinsci/plugins/pipeline/modeldefinition/WhenStageTest.java
index 93e37354b..c5215d502 100644
--- a/pipeline-model-definition/src/test/java/org/jenkinsci/plugins/pipeline/modeldefinition/WhenStageTest.java
+++ b/pipeline-model-definition/src/test/java/org/jenkinsci/plugins/pipeline/modeldefinition/WhenStageTest.java
@@ -156,8 +156,9 @@ public void whenChangeset() throws Exception {
                         "Hello",
                         "Stage \"Two\" skipped due to when conditional",
                         "Stage \"Three\" skipped due to when conditional",
+                        "Stage \"Four\" skipped due to when conditional",
                         "Warning, empty changelog. Probably because this is the first build.")
-                .logNotContains("JS World", "With regexp");
+                .logNotContains("JS World", "With regexp", "With shouldMatchAll");
         builder.go();
 
         builder.resetForNewRun(Result.SUCCESS);
@@ -168,10 +169,11 @@ public void whenChangeset() throws Exception {
         sampleRepo.git("add", "somecode.js");
         sampleRepo.git("commit", "--message=files");
 
-        builder.logContains("Hello", "JS World", "With regexp")
+        builder.logContains("Hello", "JS World", "With regexp", "With shouldMatchAll")
                 .logNotContains(
                         "Stage \"Two\" skipped due to when conditional",
                         "Stage \"Three\" skipped due to when conditional",
+                        "Stage \"Four\" skipped due to when conditional",
                         "Warning, empty changelog.",
                         "Examining changelog from all builds of this change request.")
                 .go();
@@ -185,8 +187,9 @@ public void whenChangesetMoreCommits() throws Exception {
                         "Hello",
                         "Stage \"Two\" skipped due to when conditional",
                         "Stage \"Three\" skipped due to when conditional",
+                        "Stage \"Four\" skipped due to when conditional",
                         "Warning, empty changelog. Probably because this is the first build.")
-                .logNotContains("JS World", "With regexp");
+                .logNotContains("JS World", "With regexp", "With shouldMatchAll");
         builder.go();
 
         builder.resetForNewRun(Result.SUCCESS);
@@ -210,10 +213,12 @@ public void whenChangesetMoreCommits() throws Exception {
         sampleRepo.git("add", "somefile.js");
         sampleRepo.git("commit", "--message=same");
 
-        builder.logContains("Hello", "JS World", "With regexp")
+        builder.logContains("Hello", "JS World", "With regexp",
+                            "Stage \"Four\" skipped due to when conditional")
                 .logNotContains(
                         "Stage \"Two\" skipped due to when conditional",
                         "Stage \"Three\" skipped due to when conditional",
+                        "With shouldMatchAll",
                         "Warning, empty changelog.",
                         "Examining changelog from all builds of this change request.")
                 .go();
@@ -243,8 +248,10 @@ public void whenChangesetPR() throws Exception {
         j.assertLogContains("Hello", build);
         j.assertLogContains("Stage \"Two\" skipped due to when conditional", build);
         j.assertLogContains("Stage \"Three\" skipped due to when conditional", build);
+        j.assertLogContains("With shouldMatchAll", build);
         j.assertLogNotContains("JS World", build);
         j.assertLogNotContains("With regexp", build);
+        j.assertLogNotContains("Stage \"Four\" skipped due to when conditional", build);
 
         controller.addFile("repoX", crNum,
                 "files",
@@ -258,8 +265,10 @@ public void whenChangesetPR() throws Exception {
         j.assertLogContains("Hello", build2);
         j.assertLogContains("JS World", build2);
         j.assertLogContains("With regexp", build2);
+        j.assertLogContains("With shouldMatchAll", build2);
         j.assertLogNotContains("Stage \"Two\" skipped due to when conditional", build2);
         j.assertLogNotContains("Stage \"Three\" skipped due to when conditional", build2);
+        j.assertLogNotContains("Stage \"Four\" skipped due to when conditional", build2);
         j.assertLogNotContains("Warning, empty changelog", build2);
 
         controller.addFile("repoX", crNum,
@@ -274,9 +283,11 @@ public void whenChangesetPR() throws Exception {
         j.assertLogContains("Hello", build3);
         j.assertLogContains("JS World", build3);
         j.assertLogContains("With regexp", build3);
+        j.assertLogContains("Stage \"Four\" skipped due to when conditional", build3);
         j.assertLogContains("Examining changelog from all builds of this change request", build3);
         j.assertLogNotContains("Stage \"Two\" skipped due to when conditional", build3);
         j.assertLogNotContains("Stage \"Three\" skipped due to when conditional", build3);
+        j.assertLogNotContains("With shouldMatchAll", build3);
         j.assertLogNotContains("Warning, empty changelog", build3);
     }
 
diff --git a/pipeline-model-definition/src/test/resources/json/when/conditions/changelog/changeset.json b/pipeline-model-definition/src/test/resources/json/when/conditions/changelog/changeset.json
index d4ed34538..852cb9337 100644
--- a/pipeline-model-definition/src/test/resources/json/when/conditions/changelog/changeset.json
+++ b/pipeline-model-definition/src/test/resources/json/when/conditions/changelog/changeset.json
@@ -61,6 +61,48 @@
           "value": ".*\\.js"
         }
       }]}
+    },
+    {
+      "name": "Four",
+      "branches": [      {
+        "name": "default",
+        "steps": [        {
+          "name": "echo",
+          "arguments": [          {
+            "key": "message",
+            "value":             {
+              "isLiteral": true,
+              "value": "With shouldMatchAll"
+            }
+          }]
+        }]
+      }],
+      "when": {"conditions": [      {
+        "name": "changeset",
+        "arguments":         [
+          {
+            "key": "pattern",
+            "value":             {
+              "isLiteral": true,
+              "value": "(.*\\.js|Jenkinsfile)"
+            }
+          },
+          {
+            "key": "comparator",
+            "value":             {
+              "isLiteral": true,
+              "value": "regexp"
+            }
+          },
+          {
+            "key": "shouldMatchAll",
+            "value":             {
+              "isLiteral": true,
+              "value": "true"
+            }
+          }
+        ]
+      }]}
     }
   ],
   "agent":   {
diff --git a/pipeline-model-definition/src/test/resources/when/conditions/changelog/changeset.groovy b/pipeline-model-definition/src/test/resources/when/conditions/changelog/changeset.groovy
index d29f621d4..90f40aac5 100644
--- a/pipeline-model-definition/src/test/resources/when/conditions/changelog/changeset.groovy
+++ b/pipeline-model-definition/src/test/resources/when/conditions/changelog/changeset.groovy
@@ -51,5 +51,13 @@ pipeline {
                 echo "With regexp"
             }
         }
+        stage("Four") {
+            when {
+                changeset pattern: '(.*\\.js|Jenkinsfile)', comparator: 'regexp', shouldMatchAll: true
+            }
+            steps {
+                echo "With shouldMatchAll"
+            }
+        }
     }
 }