diff --git a/packages/frontend/app/(dashboard)/components/EditCourseForm.tsx b/packages/frontend/app/(dashboard)/components/EditCourseForm.tsx
index a3d8da5f9..23cdd8f26 100644
--- a/packages/frontend/app/(dashboard)/components/EditCourseForm.tsx
+++ b/packages/frontend/app/(dashboard)/components/EditCourseForm.tsx
@@ -175,7 +175,7 @@ const EditCourseForm: React.FC<EditCourseFormProps> = ({
         <Form.Item
           label="Coordinator Email"
           name="coordinatorEmail"
-          tooltip="Email of the coordinator of the course"
+          tooltip="Email of the coordinator/instructor of the course"
           className="flex-1"
         >
           <Input allowClear={true} />
diff --git a/packages/frontend/app/(dashboard)/course/[cid]/(settings)/settings/chatbot_knowledge_base/page.tsx b/packages/frontend/app/(dashboard)/course/[cid]/(settings)/settings/chatbot_knowledge_base/page.tsx
index 11c3582dc..39f92313d 100644
--- a/packages/frontend/app/(dashboard)/course/[cid]/(settings)/settings/chatbot_knowledge_base/page.tsx
+++ b/packages/frontend/app/(dashboard)/course/[cid]/(settings)/settings/chatbot_knowledge_base/page.tsx
@@ -24,14 +24,15 @@ interface FormValues {
   content: string
   source: string
   pageNumber: string
+  name: string
 }
 
-interface ChatbotDocumentsProps {
+interface ChatbotKnowledgeBaseProps {
   params: Promise<{ cid: string }>
 }
 
-export default function ChatbotDocuments(
-  props: ChatbotDocumentsProps,
+export default function ChatbotKnowledgeBase(
+  props: ChatbotKnowledgeBaseProps,
 ): ReactElement {
   const params = use(props.params)
   const courseId = Number(params.cid)
@@ -46,14 +47,15 @@ export default function ChatbotDocuments(
   const [editRecordModalOpen, setEditRecordModalOpen] = useState(false)
   const [form] = Form.useForm()
   const [addDocChunkPopupVisible, setAddDocChunkPopupVisible] = useState(false)
+  const [dataLoading, setDataLoading] = useState(false)
 
   const addDocument = async (values: FormValues) => {
     const body: AddDocumentChunkParams = {
       documentText: values.content,
       metadata: {
-        name: 'Manually Inserted Information',
+        name: values.name || 'Manually Inserted Information',
         type: 'inserted_document',
-        source: values.source ?? undefined,
+        source: values.source || undefined,
         loc: values.pageNumber
           ? { pageNumber: parseInt(values.pageNumber) }
           : undefined,
@@ -91,6 +93,7 @@ export default function ChatbotDocuments(
 
   const fetchDocuments = useCallback(async () => {
     if (courseId) {
+      setDataLoading(true)
       await API.chatbot.staffOnly
         .getAllDocumentChunks(courseId)
         .then((response) => {
@@ -106,6 +109,7 @@ export default function ChatbotDocuments(
           message.error('Failed to load documents: ' + errorMessage)
         })
     }
+    setDataLoading(false)
   }, [courseId, setDocuments, setFilteredDocuments, search])
 
   useEffect(() => {
@@ -270,11 +274,18 @@ export default function ChatbotDocuments(
               >
                 <Input.TextArea />
               </Form.Item>
+              <Form.Item
+                label="Name"
+                name="name"
+                tooltip={`When this chunk is cited, it will show this name. Defaults to "Manually Inserted Info" if not specified.`}
+              >
+                <Input placeholder="Manually Inserted Info" />
+              </Form.Item>
               {/* <Form.Item label="Edited Chunk" name="editedChunk">
               <Input.TextArea />
             </Form.Item> */}
               <Form.Item
-                label="Source"
+                label="Source URL"
                 name="source"
                 rules={[
                   {
@@ -282,13 +293,14 @@ export default function ChatbotDocuments(
                     message: 'Please enter a valid URL',
                   },
                 ]}
-                tooltip="When a student clicks on the citation, they will be redirected to this link"
+                tooltip="When a student clicks on the citation, they will be redirected to this link. Can be a link to anything."
               >
-                <Input />
+                <Input placeholder="https://canvas.ubc.ca/courses/.../pages/..." />
               </Form.Item>
               <Form.Item
                 label="Page Number"
                 name="pageNumber"
+                tooltip="If the document in the Source URL is multi-page (e.g. a PDF), the content of the chunk should be found on this page. This is only for display purposes so that the citation says 'My doc p.3' for example. Feel free to leave this as 0 or blank."
                 rules={[
                   {
                     type: 'number',
@@ -335,6 +347,8 @@ export default function ChatbotDocuments(
         dataSource={filteredDocuments}
         size="small"
         className="w-full"
+        bordered
+        loading={documents.length === 0 && dataLoading}
         locale={{
           emptyText: (
             <Empty
diff --git a/packages/frontend/app/(dashboard)/course/[cid]/(settings)/settings/chatbot_questions/components/EditChatbotQuestionModal.tsx b/packages/frontend/app/(dashboard)/course/[cid]/(settings)/settings/chatbot_questions/components/EditChatbotQuestionModal.tsx
index e7b94bc83..3395d2ca1 100644
--- a/packages/frontend/app/(dashboard)/course/[cid]/(settings)/settings/chatbot_questions/components/EditChatbotQuestionModal.tsx
+++ b/packages/frontend/app/(dashboard)/course/[cid]/(settings)/settings/chatbot_questions/components/EditChatbotQuestionModal.tsx
@@ -72,7 +72,7 @@ const EditChatbotQuestionModal: React.FC<EditChatbotQuestionModalProps> = ({
     const newChunk: AddDocumentChunkParams = {
       documentText: values.question + '\nAnswer:' + values.answer,
       metadata: {
-        name: 'inserted Q&A',
+        name: 'Previously Asked Question',
         type: 'inserted_question',
         id: editingRecord.vectorStoreId,
         courseId: cid,
diff --git a/packages/frontend/app/(dashboard)/organization/course/add/page.tsx b/packages/frontend/app/(dashboard)/organization/course/add/page.tsx
index cc0c8a599..726dbfd76 100644
--- a/packages/frontend/app/(dashboard)/organization/course/add/page.tsx
+++ b/packages/frontend/app/(dashboard)/organization/course/add/page.tsx
@@ -227,7 +227,7 @@ export default function AddCoursePage(): ReactElement {
                     <Form.Item
                       label="Coordinator Email"
                       name="coordinatorEmail"
-                      tooltip="Email of the coordinator of the course"
+                      tooltip="Email of the coordinator/instructor of the course"
                     >
                       <Input allowClear={true} />
                     </Form.Item>
diff --git a/packages/frontend/app/(dashboard)/profile/components/AdvancedSettings.tsx b/packages/frontend/app/(dashboard)/profile/components/AdvancedSettings.tsx
new file mode 100644
index 000000000..ff7b8db83
--- /dev/null
+++ b/packages/frontend/app/(dashboard)/profile/components/AdvancedSettings.tsx
@@ -0,0 +1,14 @@
+import UserAccessTokens from './UserAccessTokens'
+import ClearProfileCache from './ClearProfileCache'
+
+const AdvancedSettings: React.FC = () => {
+  return (
+    <div className="flex w-full flex-col gap-2">
+      <h2 className="text-2xl font-bold">Advanced Settings</h2>
+      <UserAccessTokens />
+      <ClearProfileCache />
+    </div>
+  )
+}
+
+export default AdvancedSettings
diff --git a/packages/frontend/app/(dashboard)/profile/components/ClearProfileCache.tsx b/packages/frontend/app/(dashboard)/profile/components/ClearProfileCache.tsx
new file mode 100644
index 000000000..9f309908c
--- /dev/null
+++ b/packages/frontend/app/(dashboard)/profile/components/ClearProfileCache.tsx
@@ -0,0 +1,62 @@
+import { API } from '@/app/api'
+import { useUserInfo } from '@/app/contexts/userContext'
+import { getErrorMessage } from '@/app/utils/generalUtils'
+import { DeleteOutlined, QuestionCircleOutlined } from '@ant-design/icons'
+import { Button, Card, message, Tooltip } from 'antd'
+import { useState } from 'react'
+
+const ClearProfileCache: React.FC = () => {
+  const { userInfo, setUserInfo } = useUserInfo()
+  const [isLoading, setIsLoading] = useState(false)
+
+  return (
+    <>
+      {userInfo && (
+        <Card title={<h3> Profile Cache</h3>} classNames={{ body: 'py-2' }}>
+          <Tooltip
+            title={`Notice some weird behavior where the server is giving you errors but the client looks fine on your end? The profile caching may have become unsynced. Click this button to clear the cache (there are no consequences of doing so).`}
+          >
+            Clear Backend Profile Cache
+            <QuestionCircleOutlined className="ml-0.5 text-gray-500" />
+          </Tooltip>
+          <Button
+            icon={<DeleteOutlined />}
+            loading={isLoading}
+            onClick={async () => {
+              setIsLoading(true)
+              await API.profile
+                .clearCache()
+                .then(async () => {
+                  await API.profile
+                    .getUser()
+                    .then((userDetails) => {
+                      setUserInfo(userDetails)
+                      message.success(
+                        'Profile cache cleared successfully. You may want to refresh your page.',
+                      )
+                    })
+                    .catch((error) => {
+                      message.error(
+                        'Cache cleared but error getting new user details: ' +
+                          getErrorMessage(error),
+                      )
+                    })
+                })
+                .catch((error) => {
+                  message.error(
+                    'Error clearing profile cache: ' + getErrorMessage(error),
+                  )
+                })
+              setIsLoading(false)
+            }}
+            className="ml-2"
+          >
+            Clear
+          </Button>
+        </Card>
+      )}
+    </>
+  )
+}
+
+export default ClearProfileCache
diff --git a/packages/frontend/app/(dashboard)/profile/components/CoursePreference.tsx b/packages/frontend/app/(dashboard)/profile/components/CoursePreference.tsx
index 474053474..57f7bf2c0 100644
--- a/packages/frontend/app/(dashboard)/profile/components/CoursePreference.tsx
+++ b/packages/frontend/app/(dashboard)/profile/components/CoursePreference.tsx
@@ -6,7 +6,6 @@ import { getErrorMessage } from '@/app/utils/generalUtils'
 import { ExclamationCircleOutlined } from '@ant-design/icons'
 import { UserCourse } from '@koh/common'
 import { Button, message, Modal, Table, TableColumnsType } from 'antd'
-import useSWR from 'swr'
 
 const { confirm } = Modal
 
@@ -56,7 +55,11 @@ const CoursePreference: React.FC = () => {
   const InstructorCell = ({ courseId }: { courseId: number }) => {
     const course = useCourse(courseId)
 
-    return <>{course.course?.coordinator_email}</>
+    return (
+      <div className="max-w-[5.45rem] overflow-x-scroll whitespace-nowrap md:max-w-full md:overflow-x-auto">
+        {course.course?.coordinator_email}
+      </div>
+    )
   }
 
   const columns: TableColumnsType = [
diff --git a/packages/frontend/app/(dashboard)/profile/components/ProfileSettings.tsx b/packages/frontend/app/(dashboard)/profile/components/ProfileSettings.tsx
index e70e1e479..31919c8dd 100644
--- a/packages/frontend/app/(dashboard)/profile/components/ProfileSettings.tsx
+++ b/packages/frontend/app/(dashboard)/profile/components/ProfileSettings.tsx
@@ -11,7 +11,7 @@ import CoursePreference from './CoursePreference'
 import EmailNotifications from './EmailNotifications'
 import UserChatbotHistory from './UserChatbotHistory'
 import { useSearchParams } from 'next/navigation'
-import UserAccessTokens from '@/app/(dashboard)/profile/components/UserAccessTokens'
+import AdvancedSettings from './AdvancedSettings'
 
 const ProfileSettings: React.FC = () => {
   const params = useSearchParams()
@@ -24,8 +24,8 @@ const ProfileSettings: React.FC = () => {
         return SettingsOptions.PREFERENCES
       case 'chatbot_history':
         return SettingsOptions.CHATBOT_HISTORY
-      case 'access_tokens':
-        return SettingsOptions.ACCESS_TOKENS
+      case 'advanced':
+        return SettingsOptions.ADVANCED
       default:
         return SettingsOptions.PROFILE
     }
@@ -60,12 +60,10 @@ const ProfileSettings: React.FC = () => {
           {currentSettings === SettingsOptions.PREFERENCES && (
             <CoursePreference />
           )}
-          {currentSettings === SettingsOptions.ACCESS_TOKENS && (
-            <UserAccessTokens />
-          )}
           {currentSettings === SettingsOptions.CHATBOT_HISTORY && (
             <UserChatbotHistory />
           )}
+          {currentSettings === SettingsOptions.ADVANCED && <AdvancedSettings />}
         </Col>
       </Space>
     </Row>
diff --git a/packages/frontend/app/(dashboard)/profile/components/SettingsMenu.tsx b/packages/frontend/app/(dashboard)/profile/components/SettingsMenu.tsx
index d3eec86a8..ee468bd1f 100644
--- a/packages/frontend/app/(dashboard)/profile/components/SettingsMenu.tsx
+++ b/packages/frontend/app/(dashboard)/profile/components/SettingsMenu.tsx
@@ -16,6 +16,7 @@ import CoursePreference from './CoursePreference'
 import { useMediaQuery } from '@/app/hooks/useMediaQuery'
 import EmailNotifications from './EmailNotifications'
 import UserChatbotHistory from './UserChatbotHistory'
+import AdvancedSettings from './AdvancedSettings'
 
 interface SettingsMenuProps {
   currentSettings: SettingsOptions
@@ -59,6 +60,11 @@ const SettingsMenu: React.FC<SettingsMenuProps> = ({
           label: 'Chatbot History',
           children: <UserChatbotHistory />,
         },
+        {
+          key: SettingsOptions.ADVANCED,
+          label: 'Advanced',
+          children: <AdvancedSettings />,
+        },
       ]}
     />
   ) : (
@@ -88,16 +94,9 @@ const SettingsMenu: React.FC<SettingsMenuProps> = ({
           icon: <HistoryOutlined />,
         },
         {
-          key: 'Advanced',
+          key: SettingsOptions.ADVANCED,
           label: 'Advanced',
           icon: <SettingOutlined />,
-          children: [
-            {
-              key: SettingsOptions.ACCESS_TOKENS,
-              label: 'Access Tokens',
-              icon: <KeyOutlined />,
-            },
-          ],
         },
       ]}
     />
diff --git a/packages/frontend/app/(dashboard)/profile/components/UserAccessTokens.tsx b/packages/frontend/app/(dashboard)/profile/components/UserAccessTokens.tsx
index c026aaa16..df0ed0040 100644
--- a/packages/frontend/app/(dashboard)/profile/components/UserAccessTokens.tsx
+++ b/packages/frontend/app/(dashboard)/profile/components/UserAccessTokens.tsx
@@ -49,7 +49,7 @@ const UserAccessTokens: React.FC = () => {
     <div className={'flex flex-col gap-12'}>
       <Card
         title="Learning Management System Access Tokens"
-        classNames={{ body: 'flex flex-col gap-4' }}
+        classNames={{ body: 'flex flex-col gap-4', title: 'text-wrap' }}
       >
         <p>
           These are access tokens generated for learning management systems your
diff --git a/packages/frontend/app/api/index.ts b/packages/frontend/app/api/index.ts
index 894fd8459..284f81cbb 100644
--- a/packages/frontend/app/api/index.ts
+++ b/packages/frontend/app/api/index.ts
@@ -270,6 +270,8 @@ export class APIClient {
       this.req('DELETE', `/api/v1/profile/delete_profile_picture`),
     readChangelog: async (): Promise<void> =>
       this.req('PATCH', `/api/v1/profile/read_changelog`, undefined),
+    clearCache: async (): Promise<void> =>
+      this.req('DELETE', `/api/v1/profile/clear_cache`),
   }
 
   chatbot = {
@@ -720,19 +722,19 @@ export class APIClient {
       includeQueueQuestions: boolean = true,
       includeAnytimeQuestions: boolean = true,
       includeChatbotInteractions: boolean = true,
-      groupBy: 'day' | 'week' = 'week'
+      groupBy: 'day' | 'week' = 'week',
     ): Promise<ToolUsageExportData[]> => {
       const queryParams = new URLSearchParams({
         includeQueueQuestions: includeQueueQuestions.toString(),
         includeAnytimeQuestions: includeAnytimeQuestions.toString(),
         includeChatbotInteractions: includeChatbotInteractions.toString(),
-        groupBy
+        groupBy,
       })
 
       return this.req(
         'GET',
         `/api/v1/courses/${courseId}/export-tool-usage?${queryParams.toString()}`,
-        undefined
+        undefined,
       )
     },
   }
diff --git a/packages/frontend/app/typings/enum.ts b/packages/frontend/app/typings/enum.ts
index 0396fcae5..9e6ec9427 100644
--- a/packages/frontend/app/typings/enum.ts
+++ b/packages/frontend/app/typings/enum.ts
@@ -4,5 +4,5 @@ export enum SettingsOptions {
   TEAMS_SETTINGS = 'TEAMS_SETTINGS',
   PREFERENCES = 'PREFERENCES',
   CHATBOT_HISTORY = 'CHATBOT_HISTORY',
-  ACCESS_TOKENS = 'ACCESS_TOKENS',
+  ADVANCED = 'ADVANCED',
 }
diff --git a/packages/server/src/asyncQuestion/asyncQuestion.service.ts b/packages/server/src/asyncQuestion/asyncQuestion.service.ts
index 119a15143..72bb160c0 100644
--- a/packages/server/src/asyncQuestion/asyncQuestion.service.ts
+++ b/packages/server/src/asyncQuestion/asyncQuestion.service.ts
@@ -47,7 +47,7 @@ export class AsyncQuestionService {
           content: `<br> <b>${commenterIsStaff ? commenter.name : 'Someone'} has commented on your "${question.questionAbstract ?? (question.questionText ? question.questionText.slice(0, 50) : '')}" Anytime Question:</b> 
                 <br> <b>Comment Text<b>: ${comment.commentText}
                 <br>
-                <br> Note: Do NOT reply to this email. <a href="${process.env.DOMAIN}/course/${question.courseId}/async_centre">View and Reply Here</a> <br>`,
+                <br> Do NOT reply to this email. <a href="${process.env.DOMAIN}/course/${question.courseId}/async_centre"><b>View and Answer It Here</b></a> <br>`,
         })
         .catch((err) => {
           console.error(
diff --git a/packages/server/src/profile/profile.controller.ts b/packages/server/src/profile/profile.controller.ts
index 55e0acf9e..d372e5c6d 100644
--- a/packages/server/src/profile/profile.controller.ts
+++ b/packages/server/src/profile/profile.controller.ts
@@ -121,6 +121,36 @@ export class ProfileController {
   @UseInterceptors(
     FileInterceptor('file', {
       storage: memoryStorage(),
+      limits: {
+        fileSize: 5 * 1024 * 1024, // 5MB limit per file
+      },
+      fileFilter: (req, file, cb) => {
+        // Check mimetype
+        if (!file.mimetype.startsWith('image/')) {
+          cb(new Error('Only image files are allowed'), false);
+          return;
+        }
+        // Check file extension
+        const allowedExtensions = [
+          '.jpg',
+          '.jpeg',
+          '.png',
+          '.gif',
+          '.webp',
+          '.bmp',
+          '.svg',
+          '.tiff',
+          '.gif',
+        ];
+        const fileExt = file.originalname
+          .toLowerCase()
+          .substring(file.originalname.lastIndexOf('.'));
+        if (!allowedExtensions.includes(fileExt)) {
+          cb(new Error('Only image files are allowed'), false);
+          return;
+        }
+        cb(null, true);
+      },
     }),
   )
   async uploadImage(
@@ -210,4 +240,12 @@ export class ProfileController {
         .send({ message: 'Error reading changelogs' });
     }
   }
+
+  // Only 5 calls allowed in 5 minutes
+  @Throttle({ default: { limit: 5, ttl: minutes(5) } })
+  @Delete('/clear_cache')
+  @UseGuards(JwtAuthGuard, EmailVerifiedGuard)
+  async clearCache(@UserId() userId: number): Promise<void> {
+    await this.redisProfileService.deleteProfile(`u:${userId}`);
+  }
 }
diff --git a/packages/server/src/studentTaskProgress/studentTaskProgress.entity.ts b/packages/server/src/studentTaskProgress/studentTaskProgress.entity.ts
index 1f0df9581..61b1cd932 100644
--- a/packages/server/src/studentTaskProgress/studentTaskProgress.entity.ts
+++ b/packages/server/src/studentTaskProgress/studentTaskProgress.entity.ts
@@ -12,7 +12,7 @@ import { StudentTaskProgress } from '@koh/common';
 
 @Entity('student_task_progress_model')
 export class StudentTaskProgressModel extends BaseEntity {
-  @Column({ type: 'json', nullable: true })
+  @Column({ type: 'json', nullable: true }) // todo: maybe migrate this to jsonb for better querying?
   taskProgress: StudentTaskProgress; // this is the main item that this entity stores
 
   @PrimaryColumn() // two primary columns are needed to make the composite primary key (each studentTaskProgress is uniquely defined by each [cid, uid] combo)