diff --git a/core-plugins/src/e2e-test/features/groupby/GroupByWithFile.feature b/core-plugins/src/e2e-test/features/groupby/GroupByWithFile.feature
index a98adaf86..209986863 100644
--- a/core-plugins/src/e2e-test/features/groupby/GroupByWithFile.feature
+++ b/core-plugins/src/e2e-test/features/groupby/GroupByWithFile.feature
@@ -153,3 +153,156 @@ Feature: GroupBy - Verify File source to File sink data transfer using GroupBy a
     Then Close the pipeline logs
     Then Validate OUT record count of groupby is equal to IN record count of sink
     Then Validate output file generated by file sink plugin "fileSinkTargetBucket" is equal to expected output file "groupByTest3OutputFile"
+
+  @GROUP_BY_TEST @FILE_SINK_TEST
+  Scenario: To verify complete flow of data extract and transfer from File source to File sink with GroupBy plugin using MaxIf,AvgIf,SumIf,CountIf aggregates
+    Given Open Datafusion Project to configure pipeline
+    When Select plugin: "File" from the plugins list as: "Source"
+    When Expand Plugin group in the LHS plugins list: "Analytics"
+    When Select plugin: "Group By" from the plugins list as: "Analytics"
+    Then Connect plugins: "File" and "Group By" to establish connection
+    When Expand Plugin group in the LHS plugins list: "Sink"
+    When Select plugin: "File" from the plugins list as: "Sink"
+    Then Connect plugins: "Group By" and "File2" to establish connection
+    Then Navigate to the properties page of plugin: "File"
+    Then Enter input plugin property: "referenceName" with value: "FileReferenceName"
+    Then Enter input plugin property: "path" with value: "groupByTest"
+    Then Select dropdown plugin property: "format" with option value: "csv"
+    Then Click plugin property: "skipHeader"
+    Then Click on the Get Schema button
+    Then Verify the Output Schema matches the Expected Schema: "groupByCsvDataTypeFileSchema"
+    Then Validate "File" plugin properties
+    Then Close the Plugin Properties page
+    Then Navigate to the properties page of plugin: "Group By"
+    Then Select dropdown plugin property: "groupByFields" with option value: "groupByValidFirstField"
+    Then Press ESC key to close the unique fields dropdown
+    Then Select dropdown plugin property: "groupByFields" with option value: "groupByValidSecondField"
+    Then Press ESC key to close the unique fields dropdown
+    Then Enter GroupBy plugin Fields to be Aggregate "groupByFileAggregateMultipleSetFields1"
+    Then Click on the Get Schema button
+    Then Click on the Validate button
+    Then Close the Plugin Properties page
+    Then Navigate to the properties page of plugin: "File2"
+    Then Enter input plugin property: "referenceName" with value: "FileReferenceName"
+    Then Enter input plugin property: "path" with value: "fileSinkTargetBucket"
+    Then Replace input plugin property: "pathSuffix" with value: "yyyy-MM-dd-HH-mm-ss"
+    Then Select dropdown plugin property: "format" with option value: "tsv"
+    Then Validate "File2" plugin properties
+    Then Close the Plugin Properties page
+    Then Save the pipeline
+    Then Preview and run the pipeline
+    Then Wait till pipeline preview is in running state
+    Then Open and capture pipeline preview logs
+    Then Verify the preview run status of pipeline in the logs is "succeeded"
+    Then Close the pipeline logs
+    Then Close the preview
+    Then Deploy the pipeline
+    Then Run the Pipeline in Runtime
+    Then Wait till pipeline is in running state
+    Then Open and capture logs
+    Then Verify the pipeline status is "Succeeded"
+    Then Close the pipeline logs
+    Then Validate OUT record count of groupby is equal to IN record count of sink
+    Then Validate output file generated by file sink plugin "fileSinkTargetBucket" is equal to expected output file "groupByTest5OutputFile"
+
+  @GROUP_BY_TEST @FILE_SINK_TEST
+  Scenario: To verify complete flow of data extract and transfer from File source to File sink with GroupBy plugin using set of aggregates
+    Given Open Datafusion Project to configure pipeline
+    When Select plugin: "File" from the plugins list as: "Source"
+    When Expand Plugin group in the LHS plugins list: "Analytics"
+    When Select plugin: "Group By" from the plugins list as: "Analytics"
+    Then Connect plugins: "File" and "Group By" to establish connection
+    When Expand Plugin group in the LHS plugins list: "Sink"
+    When Select plugin: "File" from the plugins list as: "Sink"
+    Then Connect plugins: "Group By" and "File2" to establish connection
+    Then Navigate to the properties page of plugin: "File"
+    Then Enter input plugin property: "referenceName" with value: "FileReferenceName"
+    Then Enter input plugin property: "path" with value: "groupByTest"
+    Then Select dropdown plugin property: "format" with option value: "csv"
+    Then Click plugin property: "skipHeader"
+    Then Click on the Get Schema button
+    Then Verify the Output Schema matches the Expected Schema: "groupByCsvDataTypeFileSchema"
+    Then Validate "File" plugin properties
+    Then Close the Plugin Properties page
+    Then Navigate to the properties page of plugin: "Group By"
+    Then Select dropdown plugin property: "groupByFields" with option value: "groupByValidFirstField"
+    Then Press ESC key to close the unique fields dropdown
+    Then Select dropdown plugin property: "groupByFields" with option value: "groupByValidSecondField"
+    Then Press ESC key to close the unique fields dropdown
+    Then Enter GroupBy plugin Fields to be Aggregate "groupByFileAggregateMultipleSetFields2"
+    Then Click on the Get Schema button
+    Then Click on the Validate button
+    Then Close the Plugin Properties page
+    Then Navigate to the properties page of plugin: "File2"
+    Then Enter input plugin property: "referenceName" with value: "FileReferenceName"
+    Then Enter input plugin property: "path" with value: "fileSinkTargetBucket"
+    Then Replace input plugin property: "pathSuffix" with value: "yyyy-MM-dd-HH-mm-ss"
+    Then Select dropdown plugin property: "format" with option value: "tsv"
+    Then Validate "File2" plugin properties
+    Then Close the Plugin Properties page
+    Then Save the pipeline
+    Then Preview and run the pipeline
+    Then Wait till pipeline preview is in running state
+    Then Open and capture pipeline preview logs
+    Then Verify the preview run status of pipeline in the logs is "succeeded"
+    Then Close the pipeline logs
+    Then Close the preview
+    Then Deploy the pipeline
+    Then Run the Pipeline in Runtime
+    Then Wait till pipeline is in running state
+    Then Open and capture logs
+    Then Verify the pipeline status is "Succeeded"
+    Then Close the pipeline logs
+    Then Validate OUT record count of groupby is equal to IN record count of sink
+    Then Validate output file generated by file sink plugin "fileSinkTargetBucket" is equal to expected output file "groupByTest6OutputFile"
+
+  @GROUP_BY_TEST @FILE_SINK_TEST
+  Scenario: To verify complete flow of data extract and transfer from File source to File sink with GroupBy plugin using AnyIf and MinIf aggregates
+    Given Open Datafusion Project to configure pipeline
+    When Select plugin: "File" from the plugins list as: "Source"
+    When Expand Plugin group in the LHS plugins list: "Analytics"
+    When Select plugin: "Group By" from the plugins list as: "Analytics"
+    Then Connect plugins: "File" and "Group By" to establish connection
+    When Expand Plugin group in the LHS plugins list: "Sink"
+    When Select plugin: "File" from the plugins list as: "Sink"
+    Then Connect plugins: "Group By" and "File2" to establish connection
+    Then Navigate to the properties page of plugin: "File"
+    Then Enter input plugin property: "referenceName" with value: "FileReferenceName"
+    Then Enter input plugin property: "path" with value: "groupByTest"
+    Then Select dropdown plugin property: "format" with option value: "csv"
+    Then Click plugin property: "skipHeader"
+    Then Click on the Get Schema button
+    Then Verify the Output Schema matches the Expected Schema: "groupByCsvDataTypeFileSchema"
+    Then Validate "File" plugin properties
+    Then Close the Plugin Properties page
+    Then Navigate to the properties page of plugin: "Group By"
+    Then Select dropdown plugin property: "groupByFields" with option value: "groupByValidFirstField"
+    Then Press ESC key to close the unique fields dropdown
+    Then Select dropdown plugin property: "groupByFields" with option value: "groupByValidSecondField"
+    Then Press ESC key to close the unique fields dropdown
+    Then Enter GroupBy plugin Fields to be Aggregate "groupByFileAggregateMultipleSetFields3"
+    Then Click on the Get Schema button
+    Then Click on the Validate button
+    Then Close the Plugin Properties page
+    Then Navigate to the properties page of plugin: "File2"
+    Then Enter input plugin property: "referenceName" with value: "FileReferenceName"
+    Then Enter input plugin property: "path" with value: "fileSinkTargetBucket"
+    Then Replace input plugin property: "pathSuffix" with value: "yyyy-MM-dd-HH-mm-ss"
+    Then Select dropdown plugin property: "format" with option value: "tsv"
+    Then Validate "File2" plugin properties
+    Then Close the Plugin Properties page
+    Then Save the pipeline
+    Then Preview and run the pipeline
+    Then Wait till pipeline preview is in running state
+    Then Open and capture pipeline preview logs
+    Then Verify the preview run status of pipeline in the logs is "succeeded"
+    Then Close the pipeline logs
+    Then Close the preview
+    Then Deploy the pipeline
+    Then Run the Pipeline in Runtime
+    Then Wait till pipeline is in running state
+    Then Open and capture logs
+    Then Verify the pipeline status is "Succeeded"
+    Then Close the pipeline logs
+    Then Validate OUT record count of groupby is equal to IN record count of sink
+    Then Validate output file generated by file sink plugin "fileSinkTargetBucket" is equal to expected output file "groupByTest7OutputFile"
diff --git a/core-plugins/src/e2e-test/java/io/cdap/plugin/groupby/actions/GroupByActions.java b/core-plugins/src/e2e-test/java/io/cdap/plugin/groupby/actions/GroupByActions.java
index aa7586ee7..acbc75241 100644
--- a/core-plugins/src/e2e-test/java/io/cdap/plugin/groupby/actions/GroupByActions.java
+++ b/core-plugins/src/e2e-test/java/io/cdap/plugin/groupby/actions/GroupByActions.java
@@ -57,6 +57,9 @@ public static void enterAggregates(String jsonAggreegatesFields) {
       ElementHelper.sendKeys(GroupByLocators.field(index), entry.getKey().split("#")[0]);
       ElementHelper.selectDropdownOption(GroupByLocators.fieldFunction(index), CdfPluginPropertiesLocators.
         locateDropdownListItem(entry.getKey().split("#")[1]));
+      if (entry.getKey().split("#")[1].contains("If")) {
+        ElementHelper.sendKeys(GroupByLocators.fieldFunctionCondition(index), entry.getKey().split("#")[2]);
+      }
       ElementHelper.sendKeys(GroupByLocators.fieldFunctionAlias(index), entry.getValue());
       ElementHelper.clickOnElement(GroupByLocators.fieldAddRowButton(index));
       index++;
diff --git a/core-plugins/src/e2e-test/java/io/cdap/plugin/groupby/locators/GroupByLocators.java b/core-plugins/src/e2e-test/java/io/cdap/plugin/groupby/locators/GroupByLocators.java
index b1aa8f019..5e55d9883 100644
--- a/core-plugins/src/e2e-test/java/io/cdap/plugin/groupby/locators/GroupByLocators.java
+++ b/core-plugins/src/e2e-test/java/io/cdap/plugin/groupby/locators/GroupByLocators.java
@@ -75,4 +75,9 @@ public static WebElement addFieldsRowButton(int row) {
     String xpath = "//*[@data-cy='groupByFields']//*[@data-cy='" + row + "']//button[@data-cy='add-row']";
     return SeleniumDriver.getDriver().findElement(By.xpath(xpath));
   }
+
+  public static WebElement fieldFunctionCondition(int row) {
+    String xpath = "//div[@data-cy='aggregates']//div[@data-cy= '" + row + "']//input[@placeholder='condition']";
+    return SeleniumDriver.getDriver().findElement(By.xpath(xpath));
+  }
 }
diff --git a/core-plugins/src/e2e-test/resources/pluginParameters.properties b/core-plugins/src/e2e-test/resources/pluginParameters.properties
index f63c6cabb..bfb9065ea 100644
--- a/core-plugins/src/e2e-test/resources/pluginParameters.properties
+++ b/core-plugins/src/e2e-test/resources/pluginParameters.properties
@@ -211,6 +211,16 @@ groupByTest1OutputFile=e2e-tests/expected_outputs/CSV_GROUPBY_TEST1_Output.csv
 groupByTest2OutputFile=e2e-tests/expected_outputs/CSV_GROUPBY_TEST2_Output.csv
 groupByTest3OutputFile=e2e-tests/expected_outputs/CSV_GROUPBY_TEST3_Output.csv
 groupByMacroOutputFile=e2e-tests/expected_outputs/CSV_GROUPBY_TEST4_Output.csv
+groupByFileAggregateMultipleSetFields1=[{"key":"price#MaxIf#price>=0.50","value":"MaxIfPrice"}, \
+  {"key":"price#AvgIf#price>0.50","value":"AvgIfPrice"}, {"key":"price#SumIf#price>=0.50","value":"SumIfPrice"}, \
+  {"key":"price#CountIf#price>=0.50","value":"CountIfPrice"}]
+groupByFileAggregateMultipleSetFields2=[{"key":"price#Max","value":"MaxPrice"},\
+  {"key":"price#Sum","value":"SumPrice"},{"key":"item#Count","value":"CountItem"}]
+groupByFileAggregateMultipleSetFields3=[{"key":"price#AnyIf#price>0.6","value":"AnyIfPrice"}, \
+  {"key":"price#MinIf#price>0.35","value":"MinIfPrice"}]
+groupByTest5OutputFile=e2e-tests/expected_outputs/CSV_GROUPBY_TEST5_Output.csv
+groupByTest6OutputFile=e2e-tests/expected_outputs/CSV_GROUPBY_TEST6_Output.csv
+groupByTest7OutputFile=e2e-tests/expected_outputs/CSV_GROUPBY_TEST7_Output.csv
 ## GROUPBY-PLUGIN-PROPERTIES-END
 
 ## JOINER-PLUGIN-PROPERTIES-START
diff --git a/core-plugins/src/e2e-test/resources/testdata/expected_outputs/CSV_GROUPBY_TEST5_Output.csv b/core-plugins/src/e2e-test/resources/testdata/expected_outputs/CSV_GROUPBY_TEST5_Output.csv
new file mode 100644
index 000000000..f170fae69
--- /dev/null
+++ b/core-plugins/src/e2e-test/resources/testdata/expected_outputs/CSV_GROUPBY_TEST5_Output.csv
@@ -0,0 +1,5 @@
+bob	coffee	3.5	3.5	3.5	1
+bob	donut	2.8	1.5	1.15	3
+alice	cookie	1.4	0.8	0.7	2
+alice	tea	3.49	1.99	1.745	2
+bob	cofee	2.05	2.05	2.05	1
diff --git a/core-plugins/src/e2e-test/resources/testdata/expected_outputs/CSV_GROUPBY_TEST6_Output.csv b/core-plugins/src/e2e-test/resources/testdata/expected_outputs/CSV_GROUPBY_TEST6_Output.csv
new file mode 100644
index 000000000..0ad6de8be
--- /dev/null
+++ b/core-plugins/src/e2e-test/resources/testdata/expected_outputs/CSV_GROUPBY_TEST6_Output.csv
@@ -0,0 +1,5 @@
+bob	coffee	2	3.85	3.5
+bob	donut	4	3.25	1.5
+alice	cookie	2	1.4	0.8
+alice	tea	3	3.79	1.99
+bob	cofee	1	2.05	2.05
diff --git a/core-plugins/src/e2e-test/resources/testdata/expected_outputs/CSV_GROUPBY_TEST7_Output.csv b/core-plugins/src/e2e-test/resources/testdata/expected_outputs/CSV_GROUPBY_TEST7_Output.csv
new file mode 100644
index 000000000..450511b70
--- /dev/null
+++ b/core-plugins/src/e2e-test/resources/testdata/expected_outputs/CSV_GROUPBY_TEST7_Output.csv
@@ -0,0 +1,5 @@
+bob	coffee	3.5	3.5
+bob	donut	0.45	0.8
+alice	cookie	0.6	0.8
+alice	tea	1.5	1.99
+bob	cofee	2.05	2.05