diff --git a/airbyte-webapp/src/components/connection/ConnectionForm/SyncCatalogTable/components/StreamFieldCell.tsx b/airbyte-webapp/src/components/connection/ConnectionForm/SyncCatalogTable/components/StreamFieldCell.tsx
index 51125d80a52..83f10165569 100644
--- a/airbyte-webapp/src/components/connection/ConnectionForm/SyncCatalogTable/components/StreamFieldCell.tsx
+++ b/airbyte-webapp/src/components/connection/ConnectionForm/SyncCatalogTable/components/StreamFieldCell.tsx
@@ -22,7 +22,7 @@ import {
   isCursor as checkIsCursor,
   isPrimaryKey as checkIsPrimaryKey,
 } from "../../../syncCatalog/StreamFieldsTable/StreamFieldsTable";
-import { updateFieldSelected } from "../../../syncCatalog/SyncCatalog/streamConfigHelpers";
+import { getSelectedMandatoryFields, updateFieldSelected } from "../../../syncCatalog/SyncCatalog/streamConfigHelpers";
 import { getFieldPathDisplayName } from "../../../syncCatalog/utils";
 import { SyncStreamFieldWithId } from "../../formConfig";
 import { SyncCatalogUIModel } from "../SyncCatalogTable";
@@ -64,13 +64,11 @@ export const StreamFieldNameCell: React.FC<StreamFieldNameCellProps> = ({
   const isHashed = checkIsFieldHashed(field, config);
 
   const isDisabled =
-    !config?.selected ||
-    mode === "readonly" ||
-    (config.syncMode === SyncMode.incremental && (isCursor || isChildFieldCursor)) ||
-    (config.destinationSyncMode === DestinationSyncMode.append_dedup && (isPrimaryKey || isChildFieldPrimaryKey)) ||
-    (config.destinationSyncMode === DestinationSyncMode.overwrite_dedup && (isPrimaryKey || isChildFieldPrimaryKey)) ||
-    isNestedField;
-  const showTooltip = isDisabled && mode !== "readonly" && config?.selected;
+    config?.selected &&
+    ((config.syncMode === SyncMode.incremental && (isCursor || isChildFieldCursor)) ||
+      (config.destinationSyncMode === DestinationSyncMode.append_dedup && (isPrimaryKey || isChildFieldPrimaryKey)) ||
+      (config.destinationSyncMode === DestinationSyncMode.overwrite_dedup && (isPrimaryKey || isChildFieldPrimaryKey)));
+  const showTooltip = isDisabled && mode !== "readonly";
 
   const isFieldSelected = checkIsFieldSelected(field, config);
 
@@ -98,9 +96,15 @@ export const StreamFieldNameCell: React.FC<StreamFieldNameCellProps> = ({
       numberOfFieldsInStream,
     });
 
+    const mandatorySelectedFields = getSelectedMandatoryFields(config);
+
     updateStreamField(row.original.streamNode, {
       ...updatedConfig,
-      selectedFields: !updatedConfig?.fieldSelectionEnabled ? [] : updatedConfig?.selectedFields,
+      // any field selection immediately enables the disabled stream
+      ...(isSelected && !config?.selected && { selected: true }),
+      selectedFields: !updatedConfig?.fieldSelectionEnabled
+        ? []
+        : [...(updatedConfig?.selectedFields ?? []), ...mandatorySelectedFields],
       // remove this field if it was part of hashedFields
       hashedFields: config.hashedFields?.filter((f) => !isEqual(f.fieldPath, fieldPath)),
     });
diff --git a/airbyte-webapp/src/components/connection/ConnectionForm/SyncCatalogTable/components/StreamNameCell.tsx b/airbyte-webapp/src/components/connection/ConnectionForm/SyncCatalogTable/components/StreamNameCell.tsx
index dfeb836b8fb..ab0edbce72f 100644
--- a/airbyte-webapp/src/components/connection/ConnectionForm/SyncCatalogTable/components/StreamNameCell.tsx
+++ b/airbyte-webapp/src/components/connection/ConnectionForm/SyncCatalogTable/components/StreamNameCell.tsx
@@ -50,7 +50,14 @@ export const StreamNameCell: React.FC<StreamNameCellProps> = ({
       <CheckBox
         checkboxSize="sm"
         checked={config?.selected}
-        onChange={({ target: { checked } }) => updateStreamField(row.original.streamNode!, { selected: checked })}
+        onChange={({ target: { checked } }) =>
+          updateStreamField(row.original.streamNode!, {
+            selected: checked,
+            // enable/disable stream will enable/disable all fields
+            fieldSelectionEnabled: false,
+            selectedFields: [],
+          })
+        }
         data-testid="sync-stream-checkbox"
       />
       <Button
diff --git a/airbyte-webapp/src/components/connection/syncCatalog/SyncCatalog/streamConfigHelpers.test.ts b/airbyte-webapp/src/components/connection/syncCatalog/SyncCatalog/streamConfigHelpers.test.ts
index 47a05541e23..0d7618da558 100644
--- a/airbyte-webapp/src/components/connection/syncCatalog/SyncCatalog/streamConfigHelpers.test.ts
+++ b/airbyte-webapp/src/components/connection/syncCatalog/SyncCatalog/streamConfigHelpers.test.ts
@@ -10,6 +10,7 @@ import {
   updateCursorField,
   updateFieldSelected,
   toggleAllFieldsSelected,
+  getSelectedMandatoryFields,
 } from "./streamConfigHelpers";
 
 const FIELD_ONE: SyncSchemaField = {
@@ -405,6 +406,58 @@ describe(`${updateFieldSelected.name}`, () => {
   });
 });
 
+describe(`${getSelectedMandatoryFields.name}`, () => {
+  it("returns an empty array if the stream selected(enabled)", () => {
+    const mandatoryFields = getSelectedMandatoryFields({ ...mockStreamConfiguration, selected: true });
+    expect(mandatoryFields).toEqual([]);
+  });
+
+  it("returns an empty array if sync mode is full_refresh", () => {
+    const mandatoryFields = getSelectedMandatoryFields({
+      ...mockStreamConfiguration,
+      selected: false,
+      primaryKey: [FIELD_ONE.path, FIELD_TWO.path],
+      cursorField: FIELD_ONE.path,
+      syncMode: "full_refresh",
+    });
+
+    expect(mandatoryFields).toEqual([]);
+  });
+
+  it("returns the primary key fields if the destinationSyncMode is append_dedup", () => {
+    const mandatoryFields = getSelectedMandatoryFields({
+      ...mockStreamConfiguration,
+      selected: false,
+      primaryKey: [FIELD_ONE.path, FIELD_TWO.path],
+      destinationSyncMode: "append_dedup",
+    });
+
+    expect(mandatoryFields).toEqual([{ fieldPath: FIELD_ONE.path }, { fieldPath: FIELD_TWO.path }]);
+  });
+
+  it("returns the primary key fields if the destinationSyncMode is overwrite_dedup", () => {
+    const mandatoryFields = getSelectedMandatoryFields({
+      ...mockStreamConfiguration,
+      selected: false,
+      primaryKey: [FIELD_ONE.path, FIELD_TWO.path],
+      destinationSyncMode: "overwrite_dedup",
+    });
+
+    expect(mandatoryFields).toEqual([{ fieldPath: FIELD_ONE.path }, { fieldPath: FIELD_TWO.path }]);
+  });
+
+  it("returns the cursor field if the syncMode is incremental", () => {
+    const mandatoryFields = getSelectedMandatoryFields({
+      ...mockStreamConfiguration,
+      selected: false,
+      cursorField: FIELD_ONE.path,
+      syncMode: "incremental",
+    });
+
+    expect(mandatoryFields).toEqual([{ fieldPath: FIELD_ONE.path }]);
+  });
+});
+
 describe(`${toggleAllFieldsSelected.name}`, () => {
   it("unselects all fields if field selection was disabled", () => {
     const newStreamConfiguration = toggleAllFieldsSelected({ ...mockStreamConfiguration });
diff --git a/airbyte-webapp/src/components/connection/syncCatalog/SyncCatalog/streamConfigHelpers.ts b/airbyte-webapp/src/components/connection/syncCatalog/SyncCatalog/streamConfigHelpers.ts
index 56e38a32888..bc6626229f6 100644
--- a/airbyte-webapp/src/components/connection/syncCatalog/SyncCatalog/streamConfigHelpers.ts
+++ b/airbyte-webapp/src/components/connection/syncCatalog/SyncCatalog/streamConfigHelpers.ts
@@ -63,6 +63,27 @@ export function updateFieldSelected({
   };
 }
 
+/**
+ * If one of the fields in the disabled stream is selected,
+ * we need to ensure that mandatory fields are also selected(PK, cursor)
+ * @param config
+ */
+export const getSelectedMandatoryFields = (config: AirbyteStreamConfiguration): SelectedFieldInfo[] => {
+  const mandatoryFields: string[][] = [];
+
+  if (!config?.selected) {
+    if (config?.primaryKey?.length && ["append_dedup", "overwrite_dedup"].includes(config.destinationSyncMode)) {
+      mandatoryFields.push(...config.primaryKey);
+    }
+
+    if (config?.cursorField?.length && config.syncMode === "incremental") {
+      mandatoryFields.push(config.cursorField);
+    }
+  }
+
+  return mandatoryFields.map((fieldPath) => ({ fieldPath }));
+};
+
 interface updateFieldHashingArguments {
   config: AirbyteStreamConfiguration;
   fieldPath: string[];