diff --git a/web/src/app/admin/models/llm/LLMProviderUpdateForm.tsx b/web/src/app/admin/models/llm/LLMProviderUpdateForm.tsx
index a9ddb8e4dee..9b9b55d0187 100644
--- a/web/src/app/admin/models/llm/LLMProviderUpdateForm.tsx
+++ b/web/src/app/admin/models/llm/LLMProviderUpdateForm.tsx
@@ -222,7 +222,6 @@ export function LLMProviderUpdateForm({
                 name,
                 value: name,
               }))}
-              direction="up"
               maxHeight="max-h-56"
             />
           ) : (
@@ -246,7 +245,6 @@ export function LLMProviderUpdateForm({
                 value: name,
               }))}
               includeDefault
-              direction="up"
               maxHeight="max-h-56"
             />
           ) : (
diff --git a/web/src/app/admin/settings/SettingsForm.tsx b/web/src/app/admin/settings/SettingsForm.tsx
index 3be9e3cb7be..761eef0601a 100644
--- a/web/src/app/admin/settings/SettingsForm.tsx
+++ b/web/src/app/admin/settings/SettingsForm.tsx
@@ -51,7 +51,7 @@ function Selector({
       {label && <Label>{label}</Label>}
       {subtext && <SubLabel>{subtext}</SubLabel>}
 
-      <div className="mt-2">
+      <div className="mt-2 w-full max-w-96">
         <DefaultDropdown
           options={options}
           selected={selected}
diff --git a/web/src/app/chat/ChatPage.tsx b/web/src/app/chat/ChatPage.tsx
index 4521ecaeece..b3ccbccb7d6 100644
--- a/web/src/app/chat/ChatPage.tsx
+++ b/web/src/app/chat/ChatPage.tsx
@@ -677,6 +677,18 @@ export function ChatPage({
           {documentSidebarInitialWidth !== undefined ? (
             <Dropzone
               onDrop={(acceptedFiles) => {
+                const llmAcceptsImages = checkLLMSupportsImageInput(
+                  ...getFinalLLM(llmProviders, livePersona)
+                );
+                if (!llmAcceptsImages) {
+                  setPopup({
+                    type: "error",
+                    message:
+                      "The current Assistant does not support image input. Please select an assistant with Vision support.",
+                  });
+                  return;
+                }
+
                 uploadFilesForChat(acceptedFiles).then(([fileIds, error]) => {
                   if (error) {
                     setPopup({
@@ -690,11 +702,6 @@ export function ChatPage({
                 });
               }}
               noClick
-              disabled={
-                !checkLLMSupportsImageInput(
-                  ...getFinalLLM(llmProviders, livePersona)
-                )
-              }
               onDragLeave={() => console.log("buh")}
               onDragEnter={() => console.log("floppa")}
             >
diff --git a/web/src/app/chat/sessionSidebar/AssistantsTab.tsx b/web/src/app/chat/sessionSidebar/AssistantsTab.tsx
index 83d4a34f49f..404491961da 100644
--- a/web/src/app/chat/sessionSidebar/AssistantsTab.tsx
+++ b/web/src/app/chat/sessionSidebar/AssistantsTab.tsx
@@ -3,6 +3,7 @@ import { BasicSelectable } from "@/components/BasicClickable";
 import { User } from "@/lib/types";
 import { Text } from "@tremor/react";
 import Link from "next/link";
+import { FaRobot } from "react-icons/fa";
 import { FiEdit } from "react-icons/fi";
 
 function AssistantDisplay({
@@ -24,7 +25,9 @@ function AssistantDisplay({
       <div className="w-full" onClick={() => onSelect(persona)}>
         <BasicSelectable selected={false} fullWidth>
           <div className="flex">
-            <div className="truncate w-48 3xl:w-56">{persona.name}</div>
+            <div className="truncate w-48 3xl:w-56 flex">
+              <FaRobot className="mr-2 my-auto" size={16} /> {persona.name}
+            </div>
           </div>
         </BasicSelectable>
       </div>
@@ -54,7 +57,7 @@ export function AssistantsTab({
   const globalAssistants = personas.filter((persona) => persona.is_public);
   const personalAssistants = personas.filter(
     (persona) =>
-      !user || (persona.users.includes(user.id) && !persona.is_public)
+      (!user || persona.users.includes(user.id)) && !persona.is_public
   );
 
   return (
diff --git a/web/src/app/chat/sessionSidebar/SessionDisplay.tsx b/web/src/app/chat/sessionSidebar/SessionDisplay.tsx
index a5070f58a73..1714bd8ce00 100644
--- a/web/src/app/chat/sessionSidebar/SessionDisplay.tsx
+++ b/web/src/app/chat/sessionSidebar/SessionDisplay.tsx
@@ -156,6 +156,7 @@ export function ChatSessionDisplay({
                               />
                             </div>
                           }
+                          requiresContentPadding
                         />
                       </div>
                     </div>
diff --git a/web/src/components/Dropdown.tsx b/web/src/components/Dropdown.tsx
index 9b42ec56b3a..b88fe8693c5 100644
--- a/web/src/components/Dropdown.tsx
+++ b/web/src/components/Dropdown.tsx
@@ -286,78 +286,91 @@ export function DefaultDropdown({
   selected,
   onSelect,
   includeDefault = false,
-  direction = "down",
+  side,
   maxHeight,
 }: {
   options: StringOrNumberOption[];
   selected: string | null;
   onSelect: (value: string | number | null) => void;
   includeDefault?: boolean;
-  direction?: "up" | "down";
+  side?: "top" | "right" | "bottom" | "left";
   maxHeight?: string;
 }) {
   const selectedOption = options.find((option) => option.value === selected);
+  const [isOpen, setIsOpen] = useState(false);
+
+  const Content = (
+    <div
+      className={`
+      flex 
+      text-sm 
+      bg-background 
+      px-3
+      py-1.5 
+      rounded-lg 
+      border 
+      border-border 
+      cursor-pointer`}
+    >
+      <p className="line-clamp-1">
+        {selectedOption?.name ||
+          (includeDefault ? "Default" : "Select an option...")}
+      </p>
+      <FiChevronDown className="my-auto ml-auto" />
+    </div>
+  );
+
+  const Dropdown = (
+    <div
+      className={`
+        border 
+        border 
+        rounded-lg 
+        flex 
+        flex-col 
+        bg-background
+        ${maxHeight || "max-h-96"}
+        overflow-y-auto 
+        overscroll-contain`}
+    >
+      {includeDefault && (
+        <DefaultDropdownElement
+          key={-1}
+          name="Default"
+          onSelect={() => {
+            onSelect(null);
+          }}
+          isSelected={selected === null}
+        />
+      )}
+      {options.map((option, ind) => {
+        const isSelected = option.value === selected;
+        return (
+          <DefaultDropdownElement
+            key={option.value}
+            name={option.name}
+            description={option.description}
+            onSelect={() => onSelect(option.value)}
+            isSelected={isSelected}
+          />
+        );
+      })}
+    </div>
+  );
 
   return (
-    <CustomDropdown
-      direction={direction}
-      dropdown={
-        <div
-          className={`
-            border 
-            border 
-            rounded-lg 
-            flex 
-            flex-col 
-            bg-background
-            ${maxHeight || "max-h-96"}
-            overflow-y-auto 
-            overscroll-contain`}
-        >
-          {includeDefault && (
-            <DefaultDropdownElement
-              key={-1}
-              name="Default"
-              onSelect={() => {
-                onSelect(null);
-              }}
-              isSelected={selected === null}
-            />
-          )}
-          {options.map((option, ind) => {
-            const isSelected = option.value === selected;
-            return (
-              <DefaultDropdownElement
-                key={option.value}
-                name={option.name}
-                description={option.description}
-                onSelect={() => onSelect(option.value)}
-                isSelected={isSelected}
-              />
-            );
-          })}
-        </div>
-      }
-    >
-      <div
-        className={`
-            flex 
-            text-sm 
-            bg-background 
-            px-3
-            py-1.5 
-            rounded-lg 
-            border 
-            border-border 
-            cursor-pointer`}
-      >
-        <p className="line-clamp-1">
-          {selectedOption?.name ||
-            (includeDefault ? "Default" : "Select an option...")}
-        </p>
-        <FiChevronDown className="my-auto ml-auto" />
-      </div>
-    </CustomDropdown>
+    <div onClick={() => setIsOpen(!isOpen)}>
+      <Popover
+        open={isOpen}
+        onOpenChange={(open) => setIsOpen(open)}
+        content={Content}
+        popover={Dropdown}
+        align="start"
+        side={side}
+        sideOffset={5}
+        matchWidth
+      />
+    </div>
   );
 }
 
diff --git a/web/src/components/admin/connectors/Field.tsx b/web/src/components/admin/connectors/Field.tsx
index 825dc3ad811..39d280efd91 100644
--- a/web/src/components/admin/connectors/Field.tsx
+++ b/web/src/components/admin/connectors/Field.tsx
@@ -233,7 +233,7 @@ interface SelectorFormFieldProps {
   options: StringOrNumberOption[];
   subtext?: string | JSX.Element;
   includeDefault?: boolean;
-  direction?: "up" | "down";
+  side?: "top" | "right" | "bottom" | "left";
   maxHeight?: string;
   onSelect?: (selected: string | number | null) => void;
 }
@@ -244,7 +244,7 @@ export function SelectorFormField({
   options,
   subtext,
   includeDefault = false,
-  direction = "down",
+  side = "bottom",
   maxHeight,
   onSelect,
 }: SelectorFormFieldProps) {
@@ -262,7 +262,7 @@ export function SelectorFormField({
           selected={field.value}
           onSelect={onSelect || ((selected) => setFieldValue(name, selected))}
           includeDefault={includeDefault}
-          direction={direction}
+          side={side}
           maxHeight={maxHeight}
         />
       </div>
diff --git a/web/src/components/popover/Popover.tsx b/web/src/components/popover/Popover.tsx
index ac5d5bcf2a5..22ae839c977 100644
--- a/web/src/components/popover/Popover.tsx
+++ b/web/src/components/popover/Popover.tsx
@@ -1,5 +1,7 @@
 "use client";
 
+import "./styles.css";
+
 import * as RadixPopover from "@radix-ui/react-popover";
 
 export function Popover({
@@ -7,11 +9,21 @@ export function Popover({
   onOpenChange,
   content,
   popover,
+  side,
+  align,
+  sideOffset,
+  matchWidth,
+  requiresContentPadding,
 }: {
   open: boolean;
   onOpenChange: (open: boolean) => void;
   content: JSX.Element;
   popover: JSX.Element;
+  side?: "top" | "right" | "bottom" | "left";
+  align?: "start" | "center" | "end";
+  sideOffset?: number;
+  matchWidth?: boolean;
+  requiresContentPadding?: boolean;
 }) {
   /* 
   This Popover is needed when we want to put a popup / dropdown in a component
@@ -24,14 +36,30 @@ export function Popover({
 
   return (
     <RadixPopover.Root open={open} onOpenChange={onOpenChange}>
-      <RadixPopover.Trigger>
+      <RadixPopover.Trigger style={{ width: "100%" }}>
         {/* NOTE: this weird `-mb-1.5` is needed to offset the Anchor, otherwise 
           the content will shift up by 1.5px when the Popover is open. */}
-        {open ? <div className="-mb-1.5">{content}</div> : content}
+        {open ? (
+          <div className={requiresContentPadding ? "-mb-1.5" : ""}>
+            {content}
+          </div>
+        ) : (
+          content
+        )}
       </RadixPopover.Trigger>
-      <RadixPopover.Anchor />
       <RadixPopover.Portal>
-        <RadixPopover.Content>{popover}</RadixPopover.Content>
+        <RadixPopover.Content
+          className={
+            "PopoverContent z-[100] " +
+            (matchWidth ? " PopoverContentMatchWidth" : "")
+          }
+          asChild
+          side={side}
+          align={align}
+          sideOffset={sideOffset}
+        >
+          {popover}
+        </RadixPopover.Content>
       </RadixPopover.Portal>
     </RadixPopover.Root>
   );
diff --git a/web/src/components/popover/styles.css b/web/src/components/popover/styles.css
new file mode 100644
index 00000000000..f35957ba847
--- /dev/null
+++ b/web/src/components/popover/styles.css
@@ -0,0 +1,9 @@
+/* styles.css */
+
+.PopoverContentMatchWidth {
+  width: var(--radix-popover-trigger-width);
+}
+
+.PopoverContent[data-side="top"] {
+  transform: translateY(var(--radix-popover-trigger-height) px);
+}