Merry Mail Mystery

by Pen Stroke

Merry Mail Mystery

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The front door to the boutique opened abruptly, the little bell barely giving a single loud ring before the door was swiftly slammed shut. Then came thunderous pounding at the door as the murmur of loud voices started permeating the walls.

Having heard this cacophony, Rarity stuck her head out of her back room. She looked over the sewing glasses on the bridge of her nose, across the showroom, and towards the front door of her boutique. There she saw Ponyville’s dutiful mailmare, Derpy Hooves, breathing heavily as she fumbled to lock the door. When the door finally gave a loud click, once the firm metal bolt had slid into place, Derpy heaved a sign of relief and crumpled against the door.

Rarity took off her glasses, floating them over to her workbench before entering the showroom. “My word, what is going on?”

Derpy flinched, sat up abruptly, and looked about in panic before managing to focus one eye on Rarity. “I’m so sorry, Rarity,” she said, relaxing again at the sight of the seamstress. “I didn’t mean to barge in, but today just… It’s gotten a bit crazy.”

Rarity went over to the main window of her boutique and looked outside. Ponyville was blanketed in snow, and all nearby homes and businesses were festively decorated for the holidays. Red ribbons and green wreaths. Baubles and ornaments of various bright and shining colors. Truly, Rarity would find no place like Ponyville around Hearth’s Warming Day.

Yet the somewhat ugly, or at least stressed, side of Ponyville was showing as well. A group of ponies were standing outside her boutique. No, ‘group’ was too generous of a term. It was a festive mob decked in scarves, hats, and boots with each pony carrying what appeared to be opened cardboard boxes of various sizes.

“Crazy might be a smidge of an understatement, Darling.” Rarity said, drawing the curtains shut when one of the ponies in the mob happened to notice her looking out the window. “What in the world has them so riled up.”

Derpy got to her hooves, shaking out her wings and adjusting her festive, red and green scarf. She then turned her head, reaching into and digging around in her mailmare’s satchel. “Problems with their packages, I think. There was a lot of shouting, and I kind of panicked.” At that, Derpy drew out a package and held it out toward Rarity.

“Well, it’s certainly not in your job description to face an angry mob.” Rarity gently grasped the package, turning it over a bit. The box certainly looked in fine condition. She magically fetched some scissors from her workroom and carefully cut the tape. “And it is just a few days until Hearths Warming. I imagine some of those ponies out there were depending on their packages. Any reorders surely won’t arrive in time.”

Rarity gently drew out the contents of her package. It was a carved, clear crystal decorative tree with lots of fine detail. “Oh, it's the new centerpiece that I was going to give my mother.” Rarity began turning it over, this way and that, and the crystal was in flawless condition. She was happy, but moreover, Rarity was surprised. The packaging done by the seller was undeniably underwhelming. Just some wads of crumpled newspaper. “Were you delivering all their packages at the same time as you were delivering mine?”

“Y-yeah. I have to use the mail cart because of the number of packages I have to deliver this time of year. It’s just down the block. ” Derpy stepped closer, her forward-facing eye focusing on the tree. “Don’t tell me you’re package is damage too.”

“Don’t worry, Derpy, it’s in perfect condition.” Rarity levitated the decorative crystal tree to a flat surface, then smiled at Derpy as she went to the door. Derpy’s eyes seemed to narrow in panic as Rarity undid the lock, and she reached to stop her but was too slow. Rarity opened the door to her boutique and stepped out to meet the crowd.

“Everypony! Please, is this appropriate behavior for the holidays?” Rarity spoke loudly and confidently, and the fervor of the crowd was cut down at the knees almost immediately.

“But Rarity, she—”

Rarity stomped her hoof, causing every pony in the mob to wince. “I won’t hear a word of it. I just had the most delicate crystal centerpiece delivered to my home flawlessly by Miss Hooves. That’s despite the fact she was being chased by all of you. Now, I can appreciate the instinct to blame the mail when a package is delivered in less-than-ideal condition, but may I perhaps see some of your packages before we hurl any more accusations.”

The mob complied, the ponies nearest to Rarity setting down and pushing forward their packages. Peering down into the boxes, Rarity saw a set of festive, ceramic plates, many chipped and at least one broken. In the next box, she saw what looked to be a metal toy train set that was fairly mangled. In the last box was a set of cookie sheets, dented with one bent at an odd angle right down the middle.

Rarity then flipped closed the flaps of the boxes, looking at the exterior. The boxes themselves were pristine, with no sign of distress except for a bit of snow stuck here or there.

“Well, that is peculiar,” Rarity whispered to herself before clearing her throat and speaking to the group at large. “All right, everyone. I think I can safely say that this damage was not caused by Miss Hooves. For the kind of damage we’re seeing in the box itself, surely the exterior of the box would be just as battered. Miss Hooves also knows the packages this time of year are especially important. We all know she would never intentionally harm or act carelessly.

“Now, if any of you have fabric presents that need mending, I’d be happy to take a few minutes to try and help you. Otherwise, I know for a fact Princess Twilight has been working on a mending spell that she’d love to have some additional practice with. So, if you head to the Castle of Friendship and ask nicely, she may be able to mitigate these unfortunate holiday disasters.”

Like that the mob was diffused, some shuffling forward while others began to turn and head in the direction of Twilight’s castle. Rarity welcomed in the few that remained into her store, directing them to one corner of the shop before turning to address Derpy. “Hopefully that takes care of the worst of it, and if anyone else tries to give you grief, you can send them my way as well.”

“Oh, thank you, Rarity!”

“It’s my pleasure, Darling. But… do you have any other package to deliver after your current load?”

Derpy tilted her head to her side. “Uh… yeah, I have more waiting for me back at the post office.”

“And how much longer do you need to finish your current load?”

Derpy's eyes wander a moment, the two pupils drifting in opposite directions a moment before returning to focus. “Probably an hour.”

“Perfect. If you don’t mind, I’m going to meet you at the post office when you’re done with your current cart. I’d like a chance to examine the rest of the packages you have to deliver.”

“Wait, why do you want to do that?”

Rarity’s professional, customer service smile fell a little. “Because I would venture a guess those goods were broken before they were ever packaged.”


Derpy shivered, shaking out the cold from her limbs as she arrived back at the post office. She had finished her current load of deliveries, parked her cart, and smiled as she felt the warmth from the post office flowing over her.

“Ah, perfect timing, Derpy.”

Derpy perked up, looking over to the loading area for packages. Rarity stood there, smiling beside her boss, Parcel Post, the town’s postmaster. The light brown with dark brown maned stallion, wearing his postmaster uniform, was looking over a series of boxes that had been carefully opened and set out on the floor of the post office.

First, Derpy was a little surprised Rarity had made good on her promise to come to the post office. She imagined the famous fashionista was busy this time of year. Too busy for small-town problems. Yet, here she was all the same. Secondly, she couldn’t help but be surprised at the sight of open boxes as she walked closer to the pair. “What’s going on? I thought we weren’t ever supposed to open packages or mail?”

Parcel Post winced. He was a good boss, and he did try to give all his mail carriers some leeway and understanding. But Derpy knew that opening mail was one of the few firm rules he tried to enforce. “Yes, it is normally against regulation, but Rarity told me about the ponies chasing you this morning.”

“And after a spirited discussion, Mr. Post agreed that we should inspect more of the packages on your route for damage. After all, you shouldn’t be blamed for something that happened before the mail was entrusted to you for delivery.”

Spirited discussion. Derpy could only imagine that Rarity was sugarcoating it. She was surely one of the strongest personalities in Ponyville and was capable of getting her way through sheer force of will. Rarity was admirable like that, but also a little scary. Still, Derpy couldn’t deny it was nice to have Rarity, one of the heroes of Equestria, trying to help her out.

“Did you find anything?” Derpy asked as she leaned forward to peak in one of the open boxes.

“It’s undeniable.” Parcel Post reached into one of the boxes, pulling out a partially crumpled holiday hat. “I’d say at least half of the boxes left on your route here show some signs of damage.”

“Oh no, that’s terrible.”

“Yes, it is, but what’s odd is it’s only your route.” Rarity gestured to other piles of packages in the offices, piles designated for other mail carriers who were presently out on their deliveries. “Mr. Post says most of the other mail carriers have stopped to get their second loads for the day, and that none of them had any trouble on their routes.”

Derpy frowned. “Wait, you don’t mean… could someone have done this on purpose?”

“It’s certainly my current working theory. Yes, we have a mystery on our hooves.” Rarity’s tone was serious, but Derpy felt she couldn’t help but notice a small smile at the corner of Rarity’s mouth. “And a mystery we must solve before any more ponies can be victimized and before you, Derpy, can be further blamed.

“Mr. Post, would you be able to spare Miss Hooves for the rest of the afternoon?”

Parcel Post blinked, glancing between the two mares before shaking his head like he had just been splashed with cold water. “W-wait? What? But she still has work to do.”

“Half of what Derpy has left to deliver is damaged. Wouldn’t it be better to spend some time, to let me make use of her expertise, to find the cause of this issue? I mean, what if it starts to affect the other mail carriers?” Rarity made a dramatic gasp and closed the gap between her and Parcel Post. “What if half the town is suddenly surrounding the post office, demanding answers for why their precious holiday packages are damaged?”

Parcel Post’s eyes got a bit distant. Derpy knew that look. It was his “I’m thinking about the worst possible situation” look. It usually came out only a few times a year when Parcel’s bosses from the Equestrian Postal Service were coming for an inspection.

Parcel ran a good office. Derpy liked him as a boss, but he also ran the office in Ponyville. Since Twilight Sparkle’s arrival a few years ago, and with the need to deliver to VIPs such as the heroes of Equestria and Discord, their post office had fallen under a heightened level of scrutiny.

“Okay, I’ll… I’ll delay the broken packages a day and I’ll get some of the other carriers to handle the undamaged ones. Just… please, figure out what this is.”

Rarity smiled and tossed her mane. “Of course. Rarity and Derpy are on the case!”


“Did we need to go back to your boutique for an outfit change, Rarity?”

“Absolutely, Darling. I do my best investigative work when I’m dressed for success. And really, this outfit works so well in winter.”

Derpy followed Rarity as they returned to the post office. They had been gone fifteen minutes, Rarity stealing Derpy back to Carousel Boutique before the pair emerged in their new outfits. Rarity was wearing a trench coat with a large-rimmed hat. The coat was a dark reddish tone, the hat a darker purple, and both had accent ribbons in pink.

Derpy herself was wearing something similar, a heavier gray trenchcoat that went well with her natural color. She had also been given a dark gray bowler cap. The hat wasn't her favorite thing, but it was a really nice coat. A perfect thing to wear on a chilly day.

Derpy found it all a bit silly, but she didn’t want to question Rarity’s methods. She was a hero of Equestria for good reason.

“Now, Miss Hooves, let’s review the facts of the case as we know them.” Rarity began to walk towards the package area of the post office again. Parcel Post was at the back of the room, maneuvering and repositioning some packages in the various piles. Derpy bet that he was reshuffling the undamaged packages from her route to other carriers.

The damaged packages were still where they had been when she and Rarity left. Sitting open on the floor, showing the various damaged goods within. It was while looking at the packages that she glanced up to see Rarity was looking at her expectantly. “Oh, you want me to say the facts?”

Rarity nodded, gesturing encouragingly with a hoof.

“Right. The facts are… there were a lot of damaged packages on my route today, but none of them were damaged by me. That’s what you concluded when you talked with the mob. Then you had me meet you here, and we discovered that there were a lot of damaged packages on my route just waiting here at the post office. That means the goods were busted up before I even touched them.”

“Correct, which at the very least exonerates you, but there are now a lot of ponies with possibly ruined holiday gifts.” Rarity struck a pose, forehoof to her head. “There are still plenty of victims: the hard-working ponies of Ponyville who could receive damaged packages, holiday presents in no shape to be given. Oh, the absolute tragedy.”

Derpy had to nod her head as she moved and began to circle the boxes, using her one front-facing eye to look at the various labels on the boxes. Yes, she was happy to know she wouldn’t be blamed, but Rarity was also right. A lot of ponies could have their holidays ruined if they didn’t figure this out.

“So then we need to find more clues… right?”

Rarity smiled and nodded. “Yes, exactly, and this is where I need your expertise, Derpy. I’m afraid I know very little about how Equestria’s mail system works. Is it possible these packages were damaged en route to Ponyville?”

Derpy focused in on the box nearest to her, reaching out and grabbing one of its open flaps with her hooves. “Well, then if that were the case all of these boxes would have come from the same place. And we can know where they came from by their postmark.”

Derpy began going through the packages, checking each label, and then pulling them into a pile. In a few minutes, she had shifted the whole pile slightly a few feet from where it had been previously. “Well, they are all from the same place.”

“Excellent, and where did they come from?”

“That’s what’s confusing. They’re all from Ponyville.”

“What!?” Derpy jumped a little, turning her head around sharply and looking back to see Parcel Post rushing over towards the pair of them. “These all came through our own post office!?”

“I think so. Look, they were all postmarked yesterday.” Derpy points at various of the exposed labels.

Rarity walked over, following Depry’s pointing hoof and nodding her head. “I don’t know exactly how to read postmarks, but I do recognize the Ponyville postal code.” Rarity turned and looked at Parcel. “I don’t suppose there was anyone unusual shipping packages yesterday.”

Parcel had a deer-in-the-headlights look. “I… I don’t know. I didn’t work the front desk yesterday.”

Derpy raised a hoof, drawing Rarity and Parcel's attention. “Wait, I remember something. There were goats!”

Rarity cocked her head to one side. “Goats?”

“Yeah, I saw them yesterday when I was coming back from my lunch break. A goat was carrying a package into the office, there was one at the window mailing something, and there was another goat that was walking out.”

“Goats,” Rarity echoed again before gasping, rushing up to Derpy, and bringing their faces dangerously close together. “Were those goats perhaps wearing loose-fitting ties that were still rather complimentary in their colors?”

“Uh… oh! I do remember thinking they looked very professional. I had to wonder if maybe some new fancy business opened in town. ”

“A new business, perhaps, but I would guess it’s far from fancy.” Rarity turned sharply, tugging at the edge of her hat to pull it down a bit over her eyes. A dramatic pose, one that she held for a moment before swinging out her forehoof and causing her coat to flutter. “No, I dare say we may be dealing with a felonious enterprise of the most uncouth nature. Come, Derpy, I believe if we find and follow one of these business casual goats, we’ll find our culprits.*


“Mmmmeehhhh”

“Bbbbaaa”

“Mmeehhhh”

“That’s right, hurry up. We have more orders to fill.”

The voices coming from inside the old barn on the outskirts of Ponyville were all the confirmation Rarity needed of her suspicions. She glanced to her side, confirming Derpy was there and ready.

With a surge and flourish of her magic, Rarity threw open the doors. “Hold it right there—”

Rarity paused a moment, looking about the room before finding a blue, familiar face attached to a very tall, muscular body. She pointed her hoof accusingly and spoke with every ounce of authority her voice could muster. “Iron Will!”

The scene inside the barn resembled more a goods warehouse than anything rural. Palettes of unfolded boxes and numerous spools of packaging tape were prepared and ready near several packing tables. Numerous goats were working such tables, putting goods of various quality and condition into boxes. The goods themselves seemed to be coming from several large paletted boxes that had notably large, loud red tape around them.

“W-what!? Who are you?” Iron Will, the large, blue, muscular minotaur shouted as he strode towards Rarity and Derpy, towering over the pair of ponies. “This is a private business. You can’t just come barging here like this.”

“I’m more than aware of the sort of business you run, Mr. Will.”

“I… I don’t know who you are.”

“I am Detective Rarity! And this is my reliable assistant Miss Derpy Hooves.”

Iron Will glanced back and forth between the two before focusing back on Rarity. “Who?”

Rarity furrowed her eyebrows. “I’m a dear friend of Fluttershy and of Princess Twilight, both of which you have caused trouble for. Also, though apparently it was not meaningful enough for you to recall, you once picked me up by my horn and dropped me into a bush!”

Iron Will glanced over at Derpy. “And do I know you too?”

Derpy raised a defensive hoof and shook her head. “Oh, no, we’ve never met before.”

“Well, whether we know each other or not, this is still a private business on private property I am renting. So I am within my rights to ask both of you to leave. You're interrupting my business.

“A business of criminality!” Rarity pointed her hoof to the many packaging stations where the goats were watching with obviously damaged goods sticking out of some unsealed boxes. “You’re very obviously packaging broken merchandise and shipping it through the Equestrian Mail Service!”

“We are simply fulfilling orders.” Iron Will reached over to a nearby table and picked up a paper flyer, one that showed several festive Christmas gifts. He held out the flyer to Rarity, letting her take it in her magic. “Wonderful holiday gifts at reasonable prices sourced from entirely legitimate factory overstock auction. Really, at these prices, what more could any pony ask for this time of year?”

“I remember getting this flyer in the mail.” Rarity took, looked over, and crumpled the paper before glaring at Iron Will. “I saw this and thought it was all a joke. That it was too good to be true. Apparently, I was right.”

“It’s no joke. We are entirely fulfilling our end of the agreement. We are delivering to those ponies that ordered from us what they ordered.”

Derpy flew up in Iron Will’s face, doing her best to join Rarity in glaring him down. “But they’re broken, and they’re all on my mail route!”

Iron Will did not flinch in front of Derpy, instead planting his hooves more firmly and leaning in. “That’s just a coincidence.”

“All of your orders from your dubious flyer just happening to come from Derpy’s mail route. Why, I imagine if we go ask around town, those flyers were delivered only on Miss Hooves' route! You targeted her!”

“You have no evidence of that. All we did was distribute our limited number of flyers in areas we felt they would be most appreciated.” Iron Will took a step forward, forcing Derpy to retreat a little in the air. Another step, and now both Rarity and Derpy had to step back as they were being walked back out of the barn. “Now, I’m now officially trespassing you two. If you don’t leave I will be within my rights to escort you out—”

Iron Will stomped a hoof and flexed his muscles, voice booming loudly. “—the hard way!”

There was a moment of tension, but then Derpy began to descend. She landed next to Rarity. “Come on, Rarity. Let’s go.”

Derpy turned and started to walk out, leaving Rarity stunned in the middle. She looked at Iron Will, then Derpy, then back at Iron Will. “Uh… R-right. Yes, right behind you.”

Iron Will smiled, relaxing his pose and waiting for the mares to be at the edge of the property before he slammed the barn doors shut. Rarity flinched at the sound of the slamming doors, then turned to look at Derpy. “Now why did we leave, Derpy? Surely I could have gotten him to admit to his scheme with a little more time.”

“He already did,” Derpy said as she stopped and smiled back at Rarity. “Or, at least enough to get himself in trouble. Rarity, where did you find the flyer you said you got?”

“The flyer?” Rarity thought back, looking down at the snow a moment before the memory popped into her head. “Right, I just said I got it in the mail, didn’t I?”

Derpy smiled as she resumed walking towards town. “But I didn’t deliver any flyers on my route. So I didn’t put it in your mailbox.”

“So they delivered the flyers directly. What difference does that make?”

“Did you know it’s illegal for anypony but a certified mail carrier of Equestria to open and insert anything into a mailbox”?

Rarity stood still for a moment, her mind taking a moment to connect the dots. A grin then spread on her face as she broke into a jog to catch up to Derpy. “Oh, that is simply fascinating. I did not know that.”

“It’s something that’s not strictly enforced, but if one pony, goat, or minotaur abused it, maybe someone like Princess Twilight would like to know, right?”

Rarity felt herself grinning ear to ear. “Oh yes, I’m sure Twilight would find it fascinating. So fascinating she’d probably tell Mayor Mare, who would want to tell some town guards. And I’m sure the town guard would find it so fascinating as well. Why, by this afternoon, I imagine several guards would be out here wanting to talk to Iron Will about it.”

Derpy’s smile grew brighter and a small laugh escaped her throat. “Oh, I bet they’d be faster than that. The town guard doesn’t like anyone messing with the mail carriers. We’re the ones that bring their paychecks from Canterlot.”


Rarity heard a knock at her door, poking her head out of her backroom. It was the next day, at nearly the same time as she had heard her door being thrown open and slammed shut the day before. Having a guess who it could be, Rarity quickly set down some dress patterns she was cutting out and went to answer the door.

“Lovely to see you, Derpy,” Rarity said once she had opened the door and saw the smiling face of the dedicated mailmare on her doorstep. “Hope you’re having a better day today.”

Derpy extended her neck, holding out a small bundle of letters in her teeth. Once Rarity took them from her mouth, Derpy nodded and smiled a bit wider. “Everything’s back to normal, thanks to you, Rarity.”

“Oh, I didn’t do much, Darling.” Rarity took the letters and set them down on a table right near the door before focusing back on Derpy. “It was your expertise as a mailmare that solved most of that mystery. I just made sure you had the opportunity.”

“Well, I still appreciate it.”

“And just to let you know, the town guard did chase off Iron Will’s latest business scheme and Twilight is helping to sort out the mess he’s made. Hopefully, we’ll be able to help everyone affected before Hearth’s Warming. ”

“Oh, that’s even better.” Derpy turned, unfurling her wings. “Still, can’t stay and chat. I have a lot more mail to deliver. Happy Hearth’s Warming!”

“Happy Hearth’s Warming!” Rarity said, smiling and watching as Derpy flew off to her next house. Rarity lingered a moment, just watching the gray pegasus go about her duties before retreating into her boutique. She shut the door, picked up the stack of mail, and began to shuffle through. It was a few bills and a few payments, but among the business mail, Rarity found a festive green envelope.

Opening the envelope, Rarity pulled out a Hearth’s Warming card, one of a tree decorated in what, at first blush, looked to be bubbles. Opening the card, Rarity found a hoofwritten note inside.

Dear Rarity,

I had a lot of fun helping you solve the mystery of the damaged packages. Most of the time ponies just try to solve my problems for me, but you let me help. You let me show just how smart I can be.

If you ever want me as an assistant again, just let me know.

Happy Hearth’s Warming,
Derpy Hooves

Rarity felt the smile on her lips stretching ear to ear, and she closed the card gingerly to appreciate the decoration on the front again. She then turned, walking over and setting the card down on a particular table, one that was dotted with other Hearth’s Warming cards from her friends.

She then quickly dipped into her closet, drawing out the darker gray trench coat Derpy had worn the day before. “Such an adventure deserves a memento, and a good coat is appreciated for more than just the holidays. Hopefully Derpy won’t mind if I hoof deliver it.

“After all, I’d hate to make her deliver her own present for Hearth’s Warming.”

The End


Author's Note

Merry Jinglemas to all! Figuring out a good story for this uncommon pair of protagonists was a lot of festive fun, and I hope it was enjoyed by all, but especially by Pascoite!

Admittedly, I wasn't able to get other eyes on the story like I normally do, so notes about typoes/grammar will be greatly appreciated and promptly addressed.

Written for Pascoite for Jinglemas 2024

Cover art assembled by me from the following vector resources:
Rarity Vector by CloudGLow
Derpy Hooves Vector
Present Pile Vector
Sealed Moving Box Vector
Candy Cane Vector
Bowler Hat Vector