diff --git a/test/functional/apps/context/_filters.js b/test/functional/apps/context/_filters.js
index 470ef462b9d9d..66888d441954e 100644
--- a/test/functional/apps/context/_filters.js
+++ b/test/functional/apps/context/_filters.js
@@ -17,8 +17,6 @@
  * under the License.
  */
 
-import expect from '@kbn/expect';
-
 const TEST_INDEX_PATTERN = 'logstash-*';
 const TEST_ANCHOR_ID = 'AU_x3_BrGFA8no6QjjaI';
 const TEST_ANCHOR_FILTER_FIELD = 'geo.src';
@@ -40,20 +38,19 @@ export default function ({ getService, getPageObjects }) {
     });
 
     it('inclusive filter should be addable via expanded doc table rows', async function () {
-      await docTable.toggleRowExpanded({ isAnchorRow: true });
-
-      await retry.try(async () => {
+      await retry.waitFor(`filter ${TEST_ANCHOR_FILTER_FIELD} in filterbar`, async () => {
+        await docTable.toggleRowExpanded({ isAnchorRow: true });
         const anchorDetailsRow = await docTable.getAnchorDetailsRow();
         await docTable.addInclusiveFilter(anchorDetailsRow, TEST_ANCHOR_FILTER_FIELD);
         await PageObjects.context.waitUntilContextLoadingHasFinished();
-        expect(
-          await filterBar.hasFilter(TEST_ANCHOR_FILTER_FIELD, TEST_ANCHOR_FILTER_VALUE, true)
-        ).to.be(true);
+
+        return await filterBar.hasFilter(TEST_ANCHOR_FILTER_FIELD, TEST_ANCHOR_FILTER_VALUE, true);
+      });
+      await retry.waitFor(`filter matching docs in docTable`, async () => {
         const fields = await docTable.getFields();
-        const hasOnlyFilteredRows = fields
+        return fields
           .map((row) => row[2])
           .every((fieldContent) => fieldContent === TEST_ANCHOR_FILTER_VALUE);
-        expect(hasOnlyFilteredRows).to.be(true);
       });
     });
 
@@ -64,26 +61,27 @@ export default function ({ getService, getPageObjects }) {
       await filterBar.toggleFilterEnabled(TEST_ANCHOR_FILTER_FIELD);
       await PageObjects.context.waitUntilContextLoadingHasFinished();
 
-      await retry.try(async () => {
-        expect(
-          await filterBar.hasFilter(TEST_ANCHOR_FILTER_FIELD, TEST_ANCHOR_FILTER_VALUE, false)
-        ).to.be(true);
+      await retry.waitFor(`a disabled filter in filterbar`, async () => {
+        return await filterBar.hasFilter(TEST_ANCHOR_FILTER_FIELD, TEST_ANCHOR_FILTER_VALUE, false);
+      });
+
+      await retry.waitFor('filters are disabled', async () => {
         const fields = await docTable.getFields();
         const hasOnlyFilteredRows = fields
           .map((row) => row[2])
           .every((fieldContent) => fieldContent === TEST_ANCHOR_FILTER_VALUE);
-        expect(hasOnlyFilteredRows).to.be(false);
+        return hasOnlyFilteredRows === false;
       });
     });
 
     it('filter for presence should be addable via expanded doc table rows', async function () {
       await docTable.toggleRowExpanded({ isAnchorRow: true });
 
-      await retry.try(async () => {
+      await retry.waitFor('an exists filter in the filterbar', async () => {
         const anchorDetailsRow = await docTable.getAnchorDetailsRow();
         await docTable.addExistsFilter(anchorDetailsRow, TEST_ANCHOR_FILTER_FIELD);
         await PageObjects.context.waitUntilContextLoadingHasFinished();
-        expect(await filterBar.hasFilter(TEST_ANCHOR_FILTER_FIELD, 'exists', true)).to.be(true);
+        return await filterBar.hasFilter(TEST_ANCHOR_FILTER_FIELD, 'exists', true);
       });
     });
   });
diff --git a/test/functional/apps/context/_size.js b/test/functional/apps/context/_size.js
index 3beb070b50deb..067a23daacb4a 100644
--- a/test/functional/apps/context/_size.js
+++ b/test/functional/apps/context/_size.js
@@ -16,69 +16,69 @@
  * specific language governing permissions and limitations
  * under the License.
  */
-
-import expect from '@kbn/expect';
-
 const TEST_INDEX_PATTERN = 'logstash-*';
 const TEST_ANCHOR_ID = 'AU_x3_BrGFA8no6QjjaI';
-const TEST_DEFAULT_CONTEXT_SIZE = 7;
-const TEST_STEP_SIZE = 3;
+const TEST_DEFAULT_CONTEXT_SIZE = 2;
+const TEST_STEP_SIZE = 2;
 
 export default function ({ getService, getPageObjects }) {
   const kibanaServer = getService('kibanaServer');
   const retry = getService('retry');
   const docTable = getService('docTable');
   const PageObjects = getPageObjects(['context']);
+  let expectedRowLength = 2 * TEST_DEFAULT_CONTEXT_SIZE + 1;
 
-  // FLAKY: https://github.com/elastic/kibana/issues/53888
-  describe.skip('context size', function contextSize() {
+  describe('context size', function contextSize() {
     before(async function () {
       await kibanaServer.uiSettings.update({
         'context:defaultSize': `${TEST_DEFAULT_CONTEXT_SIZE}`,
         'context:step': `${TEST_STEP_SIZE}`,
       });
+      await PageObjects.context.navigateTo(TEST_INDEX_PATTERN, TEST_ANCHOR_ID);
     });
 
     it('should default to the `context:defaultSize` setting', async function () {
-      await PageObjects.context.navigateTo(TEST_INDEX_PATTERN, TEST_ANCHOR_ID);
-
-      await retry.try(async function () {
-        expect(await docTable.getRowsText()).to.have.length(2 * TEST_DEFAULT_CONTEXT_SIZE + 1);
-      });
-      await retry.try(async function () {
-        const predecessorCountPicker = await PageObjects.context.getPredecessorCountPicker();
-        expect(await predecessorCountPicker.getAttribute('value')).to.equal(
-          `${TEST_DEFAULT_CONTEXT_SIZE}`
-        );
-      });
-      await retry.try(async function () {
-        const successorCountPicker = await PageObjects.context.getSuccessorCountPicker();
-        expect(await successorCountPicker.getAttribute('value')).to.equal(
-          `${TEST_DEFAULT_CONTEXT_SIZE}`
-        );
-      });
+      await retry.waitFor(
+        `number of rows displayed initially is ${expectedRowLength}`,
+        async function () {
+          const rows = await docTable.getRowsText();
+          return rows.length === expectedRowLength;
+        }
+      );
+      await retry.waitFor(
+        `predecessor count picker is set to ${TEST_DEFAULT_CONTEXT_SIZE}`,
+        async function () {
+          const predecessorCountPicker = await PageObjects.context.getPredecessorCountPicker();
+          const value = await predecessorCountPicker.getAttribute('value');
+          return value === String(TEST_DEFAULT_CONTEXT_SIZE);
+        }
+      );
     });
 
     it('should increase according to the `context:step` setting when clicking the `load newer` button', async function () {
-      await PageObjects.context.navigateTo(TEST_INDEX_PATTERN, TEST_ANCHOR_ID);
       await PageObjects.context.clickPredecessorLoadMoreButton();
+      expectedRowLength += TEST_STEP_SIZE;
 
-      await retry.try(async function () {
-        expect(await docTable.getRowsText()).to.have.length(
-          2 * TEST_DEFAULT_CONTEXT_SIZE + TEST_STEP_SIZE + 1
-        );
-      });
+      await retry.waitFor(
+        `number of rows displayed after clicking load more predecessors is ${expectedRowLength}`,
+        async function () {
+          const rows = await docTable.getRowsText();
+          return rows.length === expectedRowLength;
+        }
+      );
     });
 
     it('should increase according to the `context:step` setting when clicking the `load older` button', async function () {
-      await PageObjects.context.navigateTo(TEST_INDEX_PATTERN, TEST_ANCHOR_ID);
       await PageObjects.context.clickSuccessorLoadMoreButton();
+      expectedRowLength += TEST_STEP_SIZE;
 
-      await retry.try(async function () {
-        expect(await docTable.getRowsText()).to.have.length(
-          2 * TEST_DEFAULT_CONTEXT_SIZE + TEST_STEP_SIZE + 1
-        );
-      });
+      await retry.waitFor(
+        `number of rows displayed after clicking load more successors is ${expectedRowLength}`,
+        async function () {
+          const rows = await docTable.getRowsText();
+          return rows.length === expectedRowLength;
+        }
+      );
     });
   });
 }