diff --git a/packages/code-analyzer-regex-engine/src/plugin.ts b/packages/code-analyzer-regex-engine/src/plugin.ts
index 5c5943cf..e44c3fef 100644
--- a/packages/code-analyzer-regex-engine/src/plugin.ts
+++ b/packages/code-analyzer-regex-engine/src/plugin.ts
@@ -72,7 +72,7 @@ function validateEngineName(engineName: string) {
 export function createBaseRegexRules(now: Date): RegexRules {
     return {
         NoTrailingWhitespace: {
-            regex: (/(?<target>[ \t]+)((\r?\n)|$)/g).toString(),
+            regex: (/(?<target>((?<=\S.*)[ \t]+(?=\r?\n|$))|((?<=([ \t]*\r?\n)([ \t]*\r?\n))[ \t]*\r?\n))/g).toString(),
             file_extensions: ['.cls', '.trigger'], // Currently restricted to apex files only... but we might want to extend where this rule applies in the future
             description: getMessage('TrailingWhitespaceRuleDescription'),
             violation_message: getMessage('TrailingWhitespaceRuleMessage'),
diff --git a/packages/code-analyzer-regex-engine/test/engine.test.ts b/packages/code-analyzer-regex-engine/test/engine.test.ts
index b72026d4..b852423d 100644
--- a/packages/code-analyzer-regex-engine/test/engine.test.ts
+++ b/packages/code-analyzer-regex-engine/test/engine.test.ts
@@ -268,7 +268,127 @@ describe('Tests for runRules', () => {
                     endColumn: 21
                 }]
             },
+            {
+                ruleName: "NoTrailingWhitespace",
+                message: getMessage('TrailingWhitespaceRuleMessage'),
+                primaryLocationIndex: 0,
+                codeLocations: [{
+                    file: path.resolve(__dirname, "test-data", "apexClassWhitespace", "4_multipleEmptyLines", "EmptyLinesAtEof.cls"),
+                    startLine: 7,
+                    startColumn: 1,
+                    endLine: 8,
+                    endColumn: 1
+                }]
+            },
+            {
+                ruleName: "NoTrailingWhitespace",
+                message: getMessage('TrailingWhitespaceRuleMessage'),
+                primaryLocationIndex: 0,
+                codeLocations: [{
+                    file: path.resolve(__dirname, "test-data", "apexClassWhitespace", "4_multipleEmptyLines", "MultipleEmptyLines.cls"),
+                    startLine: 6,
+                    startColumn: 1,
+                    endLine: 7,
+                    endColumn: 1
+                }]
+            },
+            {
+                ruleName: "NoTrailingWhitespace",
+                message: getMessage('TrailingWhitespaceRuleMessage'),
+                primaryLocationIndex: 0,
+                codeLocations: [{
+                    file: path.resolve(__dirname, "test-data", "apexClassWhitespace", "4_multipleEmptyLines", "EmptyLinesWithWhitespace.cls"),
+                    startLine: 6,
+                    startColumn: 1,
+                    endLine: 7,
+                    endColumn: 1
+                }]
+            },
+
+        ];
+
+        expect(runResults.violations).toHaveLength(expectedViolations.length);
+        for (const expectedViolation of expectedViolations) {
+            expect(runResults.violations).toContainEqual(expectedViolation);
+        }
+    });
+
+    it("NoTrailingWhitespace rule should flag multiple consecutive empty lines", async () => {
+        const runOptions: RunOptions = createRunOptions(
+            new Workspace('id', [path.resolve(__dirname, "test-data", "apexClassWhitespace", "4_multipleEmptyLines")]));
+        const runResults: EngineRunResults = await engine.runRules(["NoTrailingWhitespace"], runOptions);
+
+        const expectedViolations: Violation[] = [
+            {
+                ruleName: "NoTrailingWhitespace",
+                message: getMessage('TrailingWhitespaceRuleMessage'),
+                primaryLocationIndex: 0,
+                codeLocations: [{
+                    file: path.resolve(__dirname, "test-data", "apexClassWhitespace", "4_multipleEmptyLines", "MultipleEmptyLines.cls"),
+                    startLine: 6,
+                    startColumn: 1,
+                    endLine: 7,
+                    endColumn: 1
+                }]
+            },
+            {
+                ruleName: "NoTrailingWhitespace",
+                message: getMessage('TrailingWhitespaceRuleMessage'),
+                primaryLocationIndex: 0,
+                codeLocations: [{
+                    file: path.resolve(__dirname, "test-data", "apexClassWhitespace", "4_multipleEmptyLines", "EmptyLinesAtEof.cls"),
+                    startLine: 7,
+                    startColumn: 1,
+                    endLine: 8,
+                    endColumn: 1
+                }]
+            },
+            {
+                ruleName: "NoTrailingWhitespace",
+                message: getMessage('TrailingWhitespaceRuleMessage'),
+                primaryLocationIndex: 0,
+                codeLocations: [{
+                    file: path.resolve(__dirname, "test-data", "apexClassWhitespace", "4_multipleEmptyLines", "EmptyLinesWithWhitespace.cls"),
+                    startLine: 6,
+                    startColumn: 1,
+                    endLine: 7,
+                    endColumn: 1
+                }]
+            }
+        ];
+
+        expect(runResults.violations).toHaveLength(expectedViolations.length);
+        for (const expectedViolation of expectedViolations) {
+            expect(runResults.violations).toContainEqual(expectedViolation);
+        }
+    });
+
+    it("NoTrailingWhitespace rule should NOT flag single empty lines between code", async () => {
+        const runOptions: RunOptions = createRunOptions(
+            new Workspace('id', [path.resolve(__dirname, "test-data", "apexClassWhitespace", "5_singleEmptyLinesValid")]));
+        const runResults: EngineRunResults = await engine.runRules(["NoTrailingWhitespace"], runOptions);
+
+        expect(runResults.violations).toHaveLength(0);
+    });
+
+    it("NoTrailingWhitespace rule should flag multiple empty lines that contain only whitespace", async () => {
+        const runOptions: RunOptions = createRunOptions(
+            new Workspace('id', [path.resolve(__dirname, "test-data", "apexClassWhitespace", "4_multipleEmptyLines", "EmptyLinesWithWhitespace.cls")]));
+        const runResults: EngineRunResults = await engine.runRules(["NoTrailingWhitespace"], runOptions);
 
+        const expectedViolations: Violation[] = [
+            {
+                ruleName: "NoTrailingWhitespace",
+                message: getMessage('TrailingWhitespaceRuleMessage'),
+                primaryLocationIndex: 0,
+                codeLocations: [{
+                    file: path.resolve(__dirname, "test-data", "apexClassWhitespace", "4_multipleEmptyLines", "EmptyLinesWithWhitespace.cls"),
+                    startLine: 6,
+                    startColumn: 1,
+                    endLine: 7,
+                    endColumn: 1
+                }]
+            }
         ];
 
         expect(runResults.violations).toHaveLength(expectedViolations.length);
diff --git a/packages/code-analyzer-regex-engine/test/test-data/apexClassWhitespace/4_multipleEmptyLines/EmptyLinesAtEof.cls b/packages/code-analyzer-regex-engine/test/test-data/apexClassWhitespace/4_multipleEmptyLines/EmptyLinesAtEof.cls
new file mode 100644
index 00000000..145a08fd
--- /dev/null
+++ b/packages/code-analyzer-regex-engine/test/test-data/apexClassWhitespace/4_multipleEmptyLines/EmptyLinesAtEof.cls
@@ -0,0 +1,7 @@
+public class EmptyLinesAtEof {
+    public void method1() {
+        System.debug('test');
+    }
+}
+
+
diff --git a/packages/code-analyzer-regex-engine/test/test-data/apexClassWhitespace/4_multipleEmptyLines/EmptyLinesWithWhitespace.cls b/packages/code-analyzer-regex-engine/test/test-data/apexClassWhitespace/4_multipleEmptyLines/EmptyLinesWithWhitespace.cls
new file mode 100644
index 00000000..5c62bd54
--- /dev/null
+++ b/packages/code-analyzer-regex-engine/test/test-data/apexClassWhitespace/4_multipleEmptyLines/EmptyLinesWithWhitespace.cls
@@ -0,0 +1,10 @@
+public class EmptyLinesWithWhitespace {
+    public void method1() {
+        System.debug('test1');
+    }
+   
+   
+    public void method2() {
+        System.debug('test2');
+    }
+}
diff --git a/packages/code-analyzer-regex-engine/test/test-data/apexClassWhitespace/4_multipleEmptyLines/MultipleEmptyLines.cls b/packages/code-analyzer-regex-engine/test/test-data/apexClassWhitespace/4_multipleEmptyLines/MultipleEmptyLines.cls
new file mode 100644
index 00000000..1efa8698
--- /dev/null
+++ b/packages/code-analyzer-regex-engine/test/test-data/apexClassWhitespace/4_multipleEmptyLines/MultipleEmptyLines.cls
@@ -0,0 +1,10 @@
+public class MultipleEmptyLines {
+    public void method1() {
+        System.debug('test1');
+    }
+
+
+    public void method2() {
+        System.debug('test2');
+    }
+}
diff --git a/packages/code-analyzer-regex-engine/test/test-data/apexClassWhitespace/5_singleEmptyLinesValid/SingleEmptyLines.cls b/packages/code-analyzer-regex-engine/test/test-data/apexClassWhitespace/5_singleEmptyLinesValid/SingleEmptyLines.cls
new file mode 100644
index 00000000..3cdf7ff1
--- /dev/null
+++ b/packages/code-analyzer-regex-engine/test/test-data/apexClassWhitespace/5_singleEmptyLinesValid/SingleEmptyLines.cls
@@ -0,0 +1,13 @@
+public class SingleEmptyLines {
+    public void method1() {
+        System.debug('test1');
+    }
+
+    public void method2() {
+        System.debug('test2');
+    }
+
+    public void method3() {
+        System.debug('test3');
+    }
+}