diff --git a/packages/plugin-ext/src/common/plugin-api-rpc.ts b/packages/plugin-ext/src/common/plugin-api-rpc.ts
index d533974845a91..1e44cc9f44062 100644
--- a/packages/plugin-ext/src/common/plugin-api-rpc.ts
+++ b/packages/plugin-ext/src/common/plugin-api-rpc.ts
@@ -26,9 +26,9 @@ import {
     TextEditorLineNumbersStyle,
     EndOfLine,
     OverviewRulerLane,
-    IndentAction,
     FileOperationOptions,
     TextDocumentChangeReason,
+    IndentAction,
 } from '../plugin/types-impl';
 import { UriComponents } from './uri-components';
 import {
@@ -1307,19 +1307,20 @@ export interface SerializedIndentationRule {
     unIndentedLinePattern?: SerializedRegExp;
 }
 
-export interface EnterAction {
+export interface SerializedOnEnterRule {
+    beforeText: SerializedRegExp;
+    afterText?: SerializedRegExp;
+    previousLineText?: SerializedRegExp;
+    action: SerializedEnterAction;
+}
+
+export interface SerializedEnterAction {
     indentAction: IndentAction;
     outdentCurrentLine?: boolean;
     appendText?: string;
     removeText?: number;
 }
 
-export interface SerializedOnEnterRule {
-    beforeText: SerializedRegExp;
-    afterText?: SerializedRegExp;
-    action: EnterAction;
-}
-
 export interface SerializedLanguageConfiguration {
     comments?: CommentRule;
     brackets?: CharacterPair[];
diff --git a/packages/plugin-ext/src/common/plugin-protocol.ts b/packages/plugin-ext/src/common/plugin-protocol.ts
index 47fab8c9bcaca..28622bfafdec5 100644
--- a/packages/plugin-ext/src/common/plugin-protocol.ts
+++ b/packages/plugin-ext/src/common/plugin-protocol.ts
@@ -271,6 +271,7 @@ export interface PluginPackageLanguageContributionConfiguration {
     wordPattern?: string;
     indentationRules?: IndentationRules;
     folding?: FoldingRules;
+    onEnterRules?: OnEnterRule[];
 }
 
 export interface PluginTaskDefinitionContribution {
@@ -622,6 +623,7 @@ export interface LanguageConfiguration {
     comments?: CommentRule;
     folding?: FoldingRules;
     wordPattern?: string;
+    onEnterRules?: OnEnterRule[];
 }
 
 /**
@@ -670,6 +672,19 @@ export interface FoldingRules {
     markers?: FoldingMarkers;
 }
 
+export interface OnEnterRule {
+    beforeText: string;
+    afterText?: string;
+    previousLineText?: string;
+    action: EnterAction;
+}
+
+export interface EnterAction {
+    indent: 'none' | 'indent' | 'outdent' | 'indentOutdent';
+    appendText?: string;
+    removeText?: number;
+}
+
 /**
  * Custom Editors contribution
  */
diff --git a/packages/plugin-ext/src/hosted/node/scanners/scanner-theia.ts b/packages/plugin-ext/src/hosted/node/scanners/scanner-theia.ts
index 4803903e7b447..55eaa0520916d 100644
--- a/packages/plugin-ext/src/hosted/node/scanners/scanner-theia.ts
+++ b/packages/plugin-ext/src/hosted/node/scanners/scanner-theia.ts
@@ -660,7 +660,8 @@ export class TheiaPluginScanner implements PluginScanner {
                     wordPattern: rawConfiguration.wordPattern,
                     autoClosingPairs: this.extractValidAutoClosingPairs(rawLang.id, rawConfiguration),
                     indentationRules: rawConfiguration.indentationRules,
-                    surroundingPairs: this.extractValidSurroundingPairs(rawLang.id, rawConfiguration)
+                    surroundingPairs: this.extractValidSurroundingPairs(rawLang.id, rawConfiguration),
+                    onEnterRules: rawConfiguration.onEnterRules,
                 };
                 result.configuration = configuration;
             }
diff --git a/packages/plugin-ext/src/main/browser/languages-main.ts b/packages/plugin-ext/src/main/browser/languages-main.ts
index d8221e0fd7960..ebfab0c9beb41 100644
--- a/packages/plugin-ext/src/main/browser/languages-main.ts
+++ b/packages/plugin-ext/src/main/browser/languages-main.ts
@@ -1075,7 +1075,8 @@ function reviveOnEnterRule(onEnterRule: SerializedOnEnterRule): monaco.languages
     return {
         beforeText: reviveRegExp(onEnterRule.beforeText)!,
         afterText: reviveRegExp(onEnterRule.afterText),
-        action: onEnterRule.action
+        previousLineText: reviveRegExp(onEnterRule.previousLineText),
+        action: onEnterRule.action,
     };
 }
 
diff --git a/packages/plugin-ext/src/main/browser/plugin-contribution-handler.ts b/packages/plugin-ext/src/main/browser/plugin-contribution-handler.ts
index 9fb2c3f281a8d..8dc05bb00eb50 100644
--- a/packages/plugin-ext/src/main/browser/plugin-contribution-handler.ts
+++ b/packages/plugin-ext/src/main/browser/plugin-contribution-handler.ts
@@ -20,7 +20,7 @@ import { TextmateRegistry, getEncodedLanguageId, MonacoTextmateService, GrammarD
 import { MenusContributionPointHandler } from './menus/menus-contribution-handler';
 import { PluginViewRegistry } from './view/plugin-view-registry';
 import { PluginCustomEditorRegistry } from './custom-editors/plugin-custom-editor-registry';
-import { PluginContribution, IndentationRules, FoldingRules, ScopeMap, DeployedPlugin, GrammarsContribution } from '../../common';
+import { PluginContribution, IndentationRules, FoldingRules, ScopeMap, DeployedPlugin, GrammarsContribution, EnterAction, OnEnterRule } from '../../common';
 import {
     DefaultUriLabelProviderContribution,
     LabelProviderContribution,
@@ -172,7 +172,8 @@ export class PluginContributionHandler {
                         comments: langConfiguration.comments,
                         folding: this.convertFolding(langConfiguration.folding),
                         surroundingPairs: langConfiguration.surroundingPairs,
-                        indentationRules: this.convertIndentationRules(langConfiguration.indentationRules)
+                        indentationRules: this.convertIndentationRules(langConfiguration.indentationRules),
+                        onEnterRules: this.convertOnEnterRules(langConfiguration.onEnterRules),
                     }));
                 }
             }
@@ -484,7 +485,6 @@ export class PluginContributionHandler {
         }
 
         return result;
-
     }
 
     private convertTokenTypes(tokenTypes?: ScopeMap): ITokenTypeMap | undefined {
@@ -530,4 +530,42 @@ export class PluginContributionHandler {
         return result;
     }
 
+    private convertOnEnterRules(onEnterRules?: OnEnterRule[]): monaco.languages.OnEnterRule[] | undefined {
+        if (!onEnterRules) {
+            return undefined;
+        }
+
+        const result: monaco.languages.OnEnterRule[] = [];
+        for (const onEnterRule of onEnterRules) {
+            const rule: monaco.languages.OnEnterRule = {
+                beforeText: this.createRegex(onEnterRule.beforeText)!,
+                afterText: this.createRegex(onEnterRule.afterText),
+                previousLineText: this.createRegex(onEnterRule.previousLineText),
+                action: this.createEnterAction(onEnterRule.action),
+            };
+            result.push(rule);
+        }
+
+        return result;
+    }
+
+    private createEnterAction(action: EnterAction): monaco.languages.EnterAction {
+        let indentAction: monaco.languages.IndentAction;
+        switch (action.indent) {
+            case 'indent':
+                indentAction = monaco.languages.IndentAction.Indent;
+                break;
+            case 'indentOutdent':
+                indentAction = monaco.languages.IndentAction.IndentOutdent;
+                break;
+            case 'outdent':
+                indentAction = monaco.languages.IndentAction.Outdent;
+                break;
+            default:
+                indentAction = monaco.languages.IndentAction.None;
+                break;
+        }
+        return { indentAction, appendText: action.appendText, removeText: action.removeText };
+    }
+
 }
diff --git a/packages/plugin-ext/src/plugin/languages-utils.ts b/packages/plugin-ext/src/plugin/languages-utils.ts
index b429e2f99f7d1..a5f20edf7ab05 100644
--- a/packages/plugin-ext/src/plugin/languages-utils.ts
+++ b/packages/plugin-ext/src/plugin/languages-utils.ts
@@ -24,9 +24,10 @@ export function serializeEnterRules(rules?: theia.OnEnterRule[]): SerializedOnEn
 
     return rules.map(r =>
     ({
-        action: r.action,
         beforeText: serializeRegExp(r.beforeText),
-        afterText: serializeRegExp(r.afterText)
+        afterText: serializeRegExp(r.afterText),
+        previousLineText: serializeRegExp(r.previousLineText),
+        action: r.action,
     } as SerializedOnEnterRule));
 }
 
diff --git a/packages/plugin/src/theia.d.ts b/packages/plugin/src/theia.d.ts
index 0544ebd04a96f..1d518e80042c8 100644
--- a/packages/plugin/src/theia.d.ts
+++ b/packages/plugin/src/theia.d.ts
@@ -6709,6 +6709,10 @@ export module '@theia/plugin' {
          * This rule will only execute if the text after the cursor matches this regular expression.
          */
         afterText?: RegExp;
+        /**
+         * This rule will only execute if the text above the current line matches this regular expression.
+         */
+        previousLineText?: RegExp;
         /**
          * The action to execute.
          */