diff --git a/api-users.go b/api-users.go
index 51f59bd..13aa233 100644
--- a/api-users.go
+++ b/api-users.go
@@ -525,6 +525,24 @@ func (app *appContext) ExtendExpiry(gc *gin.Context) {
 		base := time.Now()
 		if expiry, ok := app.storage.GetUserExpiryKey(id); ok {
 			base = expiry.Expiry
+			app.debug.Printf(lm.FoundExistingExpiry)
+		} else if req.TryExtendFromPreviousExpiry {
+			var acts []Activity
+			app.storage.db.Find(&acts, badgerhold.Where("Type").Eq(ActivityDisabled).And("UserID").Eq(id).SortBy("Time").Reverse().Limit(1))
+			if len(acts) != 0 {
+				// Only do it if the most recent reason for disabling was expiry
+				if acts[0].SourceType == ActivityDaemon {
+					app.debug.Printf(lm.FoundPreviousExpiryLog, acts[0].Time)
+					newExpiry := acts[0].Time.AddDate(0, req.Months, req.Days).Add(time.Duration(((60 * req.Hours) + req.Minutes)) * time.Minute)
+					if newExpiry.After(base) {
+						base = acts[0].Time
+					} else {
+						app.debug.Printf(lm.ExpiryWouldBeInPast)
+					}
+				} else {
+					app.debug.Printf(lm.PreviousExpiryNotExpiry)
+				}
+			}
 		}
 		app.debug.Printf(lm.ExtendCreateExpiry, id)
 		expiry := UserExpiry{}
diff --git a/css/tooltip.css b/css/tooltip.css
index c6a193c..ab4d187 100644
--- a/css/tooltip.css
+++ b/css/tooltip.css
@@ -6,7 +6,7 @@
 .tooltip .content {
     visibility: hidden;
     opacity: 0;
-    max-width: 10rem;
+    max-width: 16rem;
     min-width: 6rem;
     background-color: rgba(0, 0, 0, 0.6);
     color: #fff;
@@ -29,6 +29,7 @@
 }
 
 .tooltip.above .content {
+    top: unset;
     bottom: calc(100% + 0.125rem);
     left: 50%;
     right: 0;
diff --git a/html/admin.html b/html/admin.html
index 8ad6dd6..580963b 100644
--- a/html/admin.html
+++ b/html/admin.html
@@ -186,56 +186,60 @@
             </form>
         </div>
         <div id="modal-extend-expiry" class="modal">
-            <form class="card relative mx-auto my-[10%] w-11/12 sm:w-4/5 lg:w-1/3" id="form-extend-expiry" href="">
+            <form class="card relative mx-auto my-[10%] w-11/12 sm:w-4/5 lg:w-1/3 flex flex-col gap-2" id="form-extend-expiry" href="">
                 <span class="heading"><span id="header-extend-expiry"></span> <span class="modal-close">&times;</span></span>
-                <div class="content mt-8">
-                    <aside class="aside sm ~urge dark:~d_info mb-2 @low row unfocused" id="extend-expiry-date"></aside>
-                    <div>
-                        <span class="text-xl supra row py-1">{{ .strings.setExpiry }}</span>
-                        <div class="row">
-                            <input type="text" id="extend-expiry-text" class="input ~neutral @low mb-2 mt-4" placeholder="{{ .strings.enterExpiry }}">
-                        </div>
+                <div class="flex flex-col gap-3">
+                    <aside class="aside sm ~urge dark:~d_info @low unfocused" id="extend-expiry-date"></aside>
+                    <div class="flex flex-col gap-2">
+                        <span class="text-xl supra">{{ .strings.setExpiry }}</span>
+                        <input type="text" id="extend-expiry-text" class="input ~neutral @low" placeholder="{{ .strings.enterExpiry }}">
                     </div>
-                    <div id="extend-expiry-field-inputs">
-                        <span class="text-xl supra row py-1">{{ .strings.extendExpiry }}</span>
-                        <div class="row">
-                            <div class="col">
+                    <div id="extend-expiry-field-inputs" class="flex flex-col gap-2">
+                        <span class="text-xl supra">{{ .strings.extendExpiry }}</span>
+                        <div class="grid grid-cols-2 grid-rows-2 gap-2">
+                            <div class="flex flex-col gap-2">
                                 <label class="label supra" for="extend-expiry-months">{{ .strings.inviteMonths }}</label>
-                                <div class="select ~neutral @low mb-2 mt-4">
+                                <div class="select ~neutral @low">
                                     <select id="extend-expiry-months">
                                         <option>0</option>
                                     </select>
                                 </div>
                             </div>
-                            <div class="col">
+                            <div class="flex flex-col gap-2">
                                 <label class="label supra" for="extend-expiry-days">{{ .strings.inviteDays }}</label>
-                                <div class="select ~neutral @low mb-2 mt-4">
+                                <div class="select ~neutral @low">
                                     <select id="extend-expiry-days">
                                         <option>0</option>
                                     </select>
                                 </div>
                             </div>
-                        </div>
-                        <div class="row">
-                            <div class="col">
+                            <div class="flex flex-col gap-2">
                                 <label class="label supra" for="extend-expiry-hours">{{ .strings.inviteHours }}</label>
-                                <div class="select ~neutral @low mb-2 mt-4">
+                                <div class="select ~neutral @low">
                                     <select id="extend-expiry-hours">
                                         <option>0</option>
                                     </select>
                                 </div>
                             </div>
-                            <div class="col">
+                            <div class="flex flex-col gap-2">
                                 <label class="label supra" for="extend-expiry-minutes">{{ .strings.inviteMinutes }}</label>
-                                <div class="select ~neutral @low mb-2 mt-4">
+                                <div class="select ~neutral @low">
                                     <select id="extend-expiry-minutes">
                                         <option>0</option>
                                     </select>
                                 </div>
                             </div>
                         </div>
+                        <label class="switch">
+                            <input type="checkbox" id="expiry-use-previous">
+                            <span>{{ .strings.extendFromPreviousExpiry }}</span>
+                            <div class="tooltip left">
+                                <i class="icon ri-information-line align-middle"></i>
+                                <div class="content sm w-max">{{ .strings.extendFromPreviousExpiryDescription }}</div>
+                            </div>
+                        </label>
                     </div>
-                    <label class="switch mb-4">
+                    <label class="switch">
                         <input type="checkbox" id="expiry-extend-enable" checked>
                         <span>{{ .strings.sendDeleteNotificationEmail }}</span>
                     </label>
diff --git a/lang/admin/en-us.json b/lang/admin/en-us.json
index 30fc673..674e85c 100644
--- a/lang/admin/en-us.json
+++ b/lang/admin/en-us.json
@@ -66,6 +66,8 @@
         "setExpiry": "Set expiry",
         "removeExpiry": "Remove expiry",
         "enterExpiry": "Enter an expiry",
+        "extendFromPreviousExpiry": "Extend from previous expiry date (if possible)",
+        "extendFromPreviousExpiryDescription": "If a record of an expired user's expiry time is found in the activity log, expiry will be extended from then, rather than the current time, unless the new expiry date would have already passed.",
         "sendPWRManual": "User {n} has no method of contact, press copy to get a link to send to them.",
         "sendPWRSuccess": "Password reset link sent.",
         "sendPWRSuccessManual": "If the user hasn't received it, press copy to get a link to manually send to them.",
diff --git a/logmessages/logmessages.go b/logmessages/logmessages.go
index 38da362..80fdf71 100644
--- a/logmessages/logmessages.go
+++ b/logmessages/logmessages.go
@@ -186,7 +186,11 @@ const (
 
 	IncorrectCaptcha = "captcha incorrect"
 
-	ExtendCreateExpiry = "Extended or created expiry for user \"%s\""
+	ExtendCreateExpiry      = "Extended or created expiry for user \"%s\""
+	FoundExistingExpiry     = "Found existing expiry key"
+	FoundPreviousExpiryLog  = "Found most recent previous expiry in activity log @ %v"
+	ExpiryWouldBeInPast     = "Expiry would've been in the past, using current time base"
+	PreviousExpiryNotExpiry = "Last user disable was not an expiry, using current time base"
 
 	UserEmailAdjusted = "Email for user \"%s\" adjusted"
 	UserAdminAdjusted = "Admin state for user \"%s\" set to %t"
diff --git a/models.go b/models.go
index 5508589..d8467e8 100644
--- a/models.go
+++ b/models.go
@@ -252,14 +252,15 @@ type customEmailDTO struct {
 }
 
 type extendExpiryDTO struct {
-	Users     []string `json:"users"`                           // List of user IDs to apply to.
-	Months    int      `json:"months" example:"1"`              // Number of months to add.
-	Days      int      `json:"days" example:"1"`                // Number of days to add.
-	Hours     int      `json:"hours" example:"2"`               // Number of hours to add.
-	Minutes   int      `json:"minutes" example:"3"`             // Number of minutes to add.
-	Timestamp int64    `json:"timestamp"`                       // Optional, exact time to expire at. Overrides other fields.
-	Notify    bool     `json:"notify"`                          // Whether to message the user(s) about the change.
-	Reason    string   `json:"reason" example:"i felt like it"` // Reason for adjustment.
+	Users                       []string `json:"users"`                                     // List of user IDs to apply to.
+	Months                      int      `json:"months,omitempty" example:"1"`              // Number of months to add.
+	Days                        int      `json:"days,omityempty" example:"1"`               // Number of days to add.
+	Hours                       int      `json:"hours,omitempty" example:"2"`               // Number of hours to add.
+	Minutes                     int      `json:"minutes,omitempty" example:"3"`             // Number of minutes to add.
+	Timestamp                   int64    `json:"timestamp,omitempty"`                       // Optional, exact time to expire at. Overrides other fields.
+	Notify                      bool     `json:"notify"`                                    // Whether to message the user(s) about the change.
+	Reason                      string   `json:"reason,omitempty" example:"i felt like it"` // Optional, reason for adjustment.
+	TryExtendFromPreviousExpiry bool     `json:"try_extend_from_previous_expiry,omitempty"` // If an activity log of the expiry of a disabled user is available, extend the expiry from that instead of the current time.
 }
 
 type checkUpdateDTO struct {
diff --git a/ts/modules/accounts.ts b/ts/modules/accounts.ts
index a4de100..8e9523d 100644
--- a/ts/modules/accounts.ts
+++ b/ts/modules/accounts.ts
@@ -836,6 +836,18 @@ interface UsersDTO extends paginatedDTO {
     users: User[];
 }
 
+declare interface ExtendExpiryDTO {
+    users: string[];
+    months?: number;
+    days?: number;
+    hours?: number;
+    minutes?: number;
+    timestamp?: number;
+    notify: boolean;
+    reason?: string;
+    try_extend_from_previous_expiry?: boolean;
+}
+
 export class accountsList extends PaginatedList {
     protected _container = document.getElementById("accounts-list") as HTMLTableSectionElement;
     
@@ -856,6 +868,7 @@ export class accountsList extends PaginatedList {
     private  _extendExpiryForm = document.getElementById("form-extend-expiry") as HTMLFormElement;
     private _extendExpiryTextInput = document.getElementById("extend-expiry-text") as HTMLInputElement;
     private _extendExpiryFieldInputs = document.getElementById("extend-expiry-field-inputs") as HTMLElement;
+    private _extendExpiryFromPreviousExpiry = document.getElementById("expiry-use-previous") as HTMLInputElement;
     private _usingExtendExpiryTextInput = true;
 
     private _extendExpiryDate = document.getElementById("extend-expiry-date") as HTMLElement;
@@ -1117,14 +1130,14 @@ export class accountsList extends PaginatedList {
         this._extendExpiryDate.classList.add("unfocused");
 
         this._extendExpiryTextInput.onkeyup = () => {
-            this._extendExpiryTextInput.parentElement.parentElement.classList.remove("opacity-60");
+            this._extendExpiryTextInput.parentElement.classList.remove("opacity-60");
             this._extendExpiryFieldInputs.classList.add("opacity-60");
                 this._usingExtendExpiryTextInput = true;
             this._displayExpiryDate();
         }
 
         this._extendExpiryTextInput.onclick = () => {
-            this._extendExpiryTextInput.parentElement.parentElement.classList.remove("opacity-60");
+            this._extendExpiryTextInput.parentElement.classList.remove("opacity-60");
             this._extendExpiryFieldInputs.classList.add("opacity-60");
             this._usingExtendExpiryTextInput = true;
             this._displayExpiryDate();
@@ -1132,15 +1145,17 @@ export class accountsList extends PaginatedList {
 
         this._extendExpiryFieldInputs.onclick = () => {
             this._extendExpiryFieldInputs.classList.remove("opacity-60");
-            this._extendExpiryTextInput.parentElement.parentElement.classList.add("opacity-60");
+            this._extendExpiryTextInput.parentElement.classList.add("opacity-60");
             this._usingExtendExpiryTextInput = false;
             this._displayExpiryDate();
         };
+
+        this._extendExpiryFromPreviousExpiry.onclick = this._displayExpiryDate;
         
         for (let field of ["months", "days", "hours", "minutes"]) {
             (document.getElementById("extend-expiry-"+field) as HTMLSelectElement).onchange = () => {
                 this._extendExpiryFieldInputs.classList.remove("opacity-60");
-                this._extendExpiryTextInput.parentElement.parentElement.classList.add("opacity-60");
+                this._extendExpiryTextInput.parentElement.classList.add("opacity-60");
                 this._usingExtendExpiryTextInput = false;
                 this._displayExpiryDate();
             };
@@ -2008,45 +2023,54 @@ export class accountsList extends PaginatedList {
     _displayExpiryDate = () => {
         let date: Date;
         let invalid = false;
+        let cantShow = false;
         let users = this._collectUsers();
         if (this._usingExtendExpiryTextInput) {
             date = (Date as any).fromString(this._extendExpiryTextInput.value) as Date;
             invalid = "invalid" in (date as any);
         } else {
-            let fields: Array<HTMLSelectElement> = [
-                document.getElementById("extend-expiry-months") as HTMLSelectElement,
-                document.getElementById("extend-expiry-days") as HTMLSelectElement,
-                document.getElementById("extend-expiry-hours") as HTMLSelectElement,
-                document.getElementById("extend-expiry-minutes") as HTMLSelectElement
-            ];
-            invalid = fields[0].value == "0" && fields[1].value == "0" && fields[2].value == "0" && fields[3].value == "0";
-            let id = users.length > 0 ? users[0] : "";
-            if (!id) invalid = true;
-            else {
-                date = new Date(this.users[id].expiry*1000);
-                if (this.users[id].expiry == 0) date = new Date();
-                date.setMonth(date.getMonth() + (+fields[0].value))
-                date.setDate(date.getDate() + (+fields[1].value));
-                date.setHours(date.getHours() + (+fields[2].value));
-                date.setMinutes(date.getMinutes() + (+fields[3].value));
+            if (this._extendExpiryFromPreviousExpiry.checked) {
+                cantShow = true;
+            } else {
+                let fields: Array<HTMLSelectElement> = [
+                    document.getElementById("extend-expiry-months") as HTMLSelectElement,
+                    document.getElementById("extend-expiry-days") as HTMLSelectElement,
+                    document.getElementById("extend-expiry-hours") as HTMLSelectElement,
+                    document.getElementById("extend-expiry-minutes") as HTMLSelectElement
+                ];
+                invalid = fields[0].value == "0" && fields[1].value == "0" && fields[2].value == "0" && fields[3].value == "0";
+                let id = users.length > 0 ? users[0] : "";
+                if (!id) invalid = true;
+                else {
+                    date = new Date(this.users[id].expiry*1000);
+                    if (this.users[id].expiry == 0) date = new Date();
+                    date.setMonth(date.getMonth() + (+fields[0].value))
+                    date.setDate(date.getDate() + (+fields[1].value));
+                    date.setHours(date.getHours() + (+fields[2].value));
+                    date.setMinutes(date.getMinutes() + (+fields[3].value));
+                }
             }
         }
         const submit = this._extendExpiryForm.querySelector(`input[type="submit"]`) as HTMLInputElement;
         const submitSpan = submit.nextElementSibling;
+        if (invalid || cantShow) {
+            this._extendExpiryDate.classList.add("unfocused");
+        }
         if (invalid) {
             submit.disabled = true;
             submitSpan.classList.add("opacity-60");
-            this._extendExpiryDate.classList.add("unfocused");
         } else {
             submit.disabled = false;
             submitSpan.classList.remove("opacity-60");
-            this._extendExpiryDate.innerHTML = `
-            <div class="flex flex-col">
-                <span>${window.lang.strings("accountWillExpire").replace("{date}", toDateString(date))}</span>
-                ${users.length > 1 ? "<span>"+window.lang.strings("expirationBasedOn")+"</span>" : ""}
-            </div>
-            `;
-            this._extendExpiryDate.classList.remove("unfocused");
+            if (!cantShow) {
+                this._extendExpiryDate.innerHTML = `
+                <div class="flex flex-col">
+                    <span>${window.lang.strings("accountWillExpire").replace("{date}", toDateString(date))}</span>
+                    ${users.length > 1 ? "<span>"+window.lang.strings("expirationBasedOn")+"</span>" : ""}
+                </div>
+                `;
+                this._extendExpiryDate.classList.remove("unfocused");
+            }
         }
     }
 
@@ -2072,18 +2096,25 @@ export class accountsList extends PaginatedList {
         }
         document.getElementById("header-extend-expiry").textContent = header;
         const extend = () => {
-            let send = { "users": applyList, "timestamp": 0, "notify": this._enableExpiryNotify.checked }
+            let send: ExtendExpiryDTO = {
+                users: applyList,
+                timestamp: 0,
+                notify: this._enableExpiryNotify.checked
+            }
             if (this._enableExpiryNotify.checked) {
-                send["reason"] = this._enableExpiryReason.value;
+                send.reason = this._enableExpiryReason.value;
             }
             if (this._usingExtendExpiryTextInput) {
                 let date = (Date as any).fromString(this._extendExpiryTextInput.value) as Date;
-                send["timestamp"] = Math.floor(date.getTime() / 1000);
+                send.timestamp = Math.floor(date.getTime() / 1000);
                 if ("invalid" in (date as any)) {
                     window.notifications.customError("extendExpiryError", window.lang.notif("errorInvalidDate"));
                     return;
                 }
             } else {
+                if (this._extendExpiryFromPreviousExpiry.checked) {
+                    send.try_extend_from_previous_expiry = true;
+                }
                 for (let field of ["months", "days", "hours", "minutes"]) {
                     send[field] = +(document.getElementById("extend-expiry-"+field) as HTMLSelectElement).value;
                 }